Синтез и модификация морфинановых и родственных систем: металлоорганический подход

Список литературы

1. Chida N. Recent advances in the synthesis of morphine and related alkaloids.
2. In: Topics in Current Chemistry. 299. Chemistry of Opioids. — Nagase H. (Ed.) Springer, Berlin-Heidelberg. — 2011. — 312 pp. — P. 1−28
3. Калинин B.H., Кобелысова Н. И. Металлоорганические соединения вхимии морфиновых алкалоидов. // Ж. Всес. хим. общ. 1991. — Т. 26. -С. 443−447
4. Mulzer J., Diirner G., Trauner D. Formal total synthesis of (-)-morphine bycuprate conjugate addition. // Angew. Chem. Int. Ed. (Engl.) 1996. — V. 35.-P. 2830−2832
5. Trauner D., Bats J.W., Werner A., Mulzer J. Synthesis of enantiomerically pure morphine alkaloids: the hydrophenanthrene route. // J. Org. Chem. -1998.-V. 63.-P. 5908−5918
6. Mulzer J., Trauner D. Practical synthesis of (-)-morphine. // Chirality. 1999.-V. 11.-P. 475−482
7. White J.D., Hrnciar P., Stappenbeck F. Asymmetric total synthesis of (+)-codeine via intramolecular carbenoid insertion. // J. Org. Chem. 1999. — V. 64.-P. 7871−7884
8. Trost B.M., Tang W. Enantioselective synthesis of (-)-codeine and (-)morphine. // J. Amer. Chem. Soc. 2002. — V. 124. — P. 14 542−14 543
9. Organometallics in Process Chemistry. Larsen R.D. (Ed.) — Springer, 1. Berlin. 2004
10. Torborg C., Beller M. Recent applications of palladium-catalyzed couplingreactions in the pharmaceutical, agrochemical, and fine chemical industries. // Adv. Synth. Catal. 2009. — V. 351. — P. 3027−3043
11. Corbet J.-P., Mignani G. Selected patented cross-coupling reaction technologies. // Chem. Rev. 2006. — V. 106. — P. 2651−2710
12. Pert C.B., Snyder S.H. Opiate receptor: demonstration in nervous tissue. //
13. Science. 1973. — V. 179. — P. 1011−1014
14. Simon E.J., Hiller J.M., Edelman I. Stereospecific binding of the potent narcotic analgesic (3H) etorphine to rat-brain homogenate. // Proc. Natl. Acad. Sci. U.S.A. 1973. -V. 70. — P. 1947−1949
15. Terenius L. Stereospecific interaction between narcotic analgesics and a synaptic membrane fraction of rat cerebral cortex. // Acta Pharmacol. Toxicol. 1973. — V. 32. — P. 317−320
16. Casy A.F., Parfitt R.T. Opioid analgesics. Chemistry and receptors. -Plenum Press. New York, London. — 1986
17. Hughes J. Isolation of an endogenous compound from the brain with pharmacological properties similar to morphine. // Brain Res. 1975. — V. 88.-P. 295−308
18. Pasternak G.W., Goodman R., Snyder S.H. An endogenous morphine-likefactor in mammalian brain. // Life Sci. 1975. — V. 16. — P. 1765
19. Terenius L., Wahlstrom A. Search for an endogenous ligand for the opiatereceptor. // Acta Physiol. Scand. 1975. — V. 94. — P. 74−81
20. Teschemacher H., Opheim K.E., Cox B.M., Goldstein A. A peptide-like substance from pituitary that acts like morphine. Isolation. // Life Sci. -1975.-V. 16.-P. 1771−1775
21. Cox B.M., Teschemacher H., Opheim K.E., Goldstein A. A peptide-like substance from pituitary that acts like morphine. Purification and properties. //Life Sci. 1975. -V. 16. — P. 1777−1782
22. Hughes J., Smith T.W., Kosterlitz H.W., Fothergill L.A., Morgan B.A., Morris H.R. Identification of two related pentapeptides from the brain with potent opiate agonist activity. // Nature. 1975. — V. 258. — P. 577−579 506
23. Cox B.M. Endogenous opioid peptides: a guide to structures and terminology. //Life Sci. 1982.- V. 31.-P. 1645−1658
24. Zadina J.E., Hackler L., Ge L.-J., Kastin A.J. A potent and selective endogenous ligand for the /?-opiate receptor. // Nature. 1997. — V. 386. -P. 499−502
25. Goldstein A., Fischli W., Lowney L.I., Hunkapiller M., Hood L. Porcine pituitary dynorphin: complete amino acid sequence of the biologically active heptadecapeptide. // Proc. Natl. Acad. Sci. U.S.A. 1981. — V. 78. -P. 7219−7223
26. Portoghese P. S. From models to molecules: opioid receptor dimers, bivalentligands, and selective opioid receptor probes. // J. Med. Chem. 2001. — V. 44. — P. 2259−2269
27. Martin W.R., Eades C.G., Thompson J.A., Huppler R.E., Gilbert P.E. Theeffects of morphine- and nalorphine-like drugs in the nondependent and morphine-dependent chronic spinal dog. // J. Pharmacol. Exp. Ther. 1976. -V. 197.-P. 517−532
28. Lord J.A.H., Waterfield A.A., Hughes J., Kosterlitz H.W. Endogenous opioid peptides: multiple agonists and receptors. // Nature. 1977. — V. 267.-P. 495−499
29. Law P.Y., Wong Y.H., Loh H.H. Molecular mechanisms and regulation ofopioid receptor signaling. // Annu. Rev. Pharmacol. Toxicol. 2000. — V. 40. P. 389−430
30. Lenz G.R., Evans S.M., Walters D.E., Hopfinger A.J. Opiates. Academic
31. Press. Orlando, London. — 1986
32. Evans C.J., Keith D.E., Jr., Morrison H., Magendzo K., Edwards R. H. Cloning of a delta opioid receptor by functional expression. // Science. -1992. V. 258. — P. 1952−1955
33. Kieffer B.L., Befort K., Gaveriaux-Ruff C., Hirth C.G. The ?-opioid receptor: isolation of a cDNA by expression cloning and pharmacological characterization. // Proc. Natl. Acad. Sci. U.S.A. 1992. — V. 89. — P. 12 048−12 052
34. Yasuda K., Raynor K., Kong H., Breder C.D., Takeda J., Reisine T., Bell G.I. Cloning and functional comparison of k and 8 opioid receptors from mouse brain. // Proc. Natl. Acad. Sci. U.S.A. 1993. — V. 90. — P. 67 366 740
35. Wang J.B., Imai Y., Eppler M., Gregor P., Spivak C.E., Uhl G.R. /?-Opiate receptor: cDNA cloning and expression. // Proc. Natl. Acad. Sci. U.S.A. -1993.-V. 90.-P. 10 230−10 234
36. Wang J.B., Johnson P. S., Imai Y., Persico A.M., Ozenberger B.A., Eppler C.M., Uhl G.R. cDNA cloning of an orphan opiate receptor gene family member and its splice variant. // FEBS Lett. 1994. — V. 348. — P. 75−79
37. Fukuda K., Kato S., Mori K., Nishi M., Takeshima H. Primary structures and expression from cDNAs of rat opioid receptor S and /?-subtypes. // FEBS Lett. 1993. -V. 327. — P. 311−314
38. Knapp R.J., Malatynska E., Fang L., Li X., Babin E., Nguyen M., Santoro
39. G., Varga E.V., Hruby V.J., Roeske W.R., Yamamura H.I. Identification of a human delta opioid receptor: cloning and expression. // Life Sci. 1994. -V. 54.-P. 463−469
40. Mansson E., Bare L., Yang D. Isolation of a human H opioid receptor cDNAfrom placenta. // Biochem. Biophys. Res. Commun. 1994. — V. 202. — P. 1431−1437
41. Reisine T. Opiate receptors. // Neuropharmacology. 1995. — V. 34. — P. 463−472
42. Thompson R.C., Mansour A., Akil H., Watson S.J. Cloning and pharmacological characterization of a rat mu opioid receptor. // Neuron. -1993.-V. 11.-P. 903−913
43. Meng F., Xie G.X., Thompson R.C., Mansour A., Goldstein A., Watson S.J.,
44. Akil H. Cloning and pharmacological characterization of a rat kappa opioid receptor. // Proc. Natl. Acad .Sci. U.S.A. 1993. — V. 90. — P. 9954−9958
45. Molleaau C., Parmentier M., Mailleux P., Butour J., Moisand C., Chalon P.,
46. Caput D., Vassart G., Meunier J.-C. ORL-1, a novel member of the opioid receptor family. Cloning, functional expression and localization. // FEBS Lett. 1994. — V. 341. — P. 33−38
47. Fukuda K., Kato S., Mori K., Nishi M., Takeshima H., Iwabe N., Miyata T.,
48. Houtani T., Sugimoto T. cDNA cloning and regional distribution of a novel member of the opioid receptor family. // FEBS Lett. 1994. — V. 343. — P. 42−46
49. Chen Y., Fan Y., Liu J., Mestek A., Tian M., Kozak C.A., Yu L. Molecularcloning, tissue distribution and chromosomal localization of a novel member of the opioid receptor gene family. // FEBS Lett. 1994. — V. 347. — P. 279−283
50. Reinsceid R.K., Nothacker H.-P., Bourson A., Ardati A., Henningsen R.A.,
51. Bunzow J.R., Grady D.K., Langen H., Monsma F.J., Jr., Civelli O. Orphanin FQ: a neuropeptide that activates an opioid like G protein-coupled receptor. // Science. 1995. — V. 270. — P. 792−794
52. Meunier J.-C., Mollereau C., Toll L., Suaudeu C., Moisand C., Alvinerie P.,
53. Butour J.-L., Guillemot J.-C., Ferrara P., Monsarrat B., Mazarguil H.,
54. Vassart G., Parmentier M., Constentin J. Isolation and structure of the endogenous agonist of opioid receptor-like ORL-1 receptor. // Nature. -1995.-V. 377.-P. 532−535
55. Mansour A., Watson S.J. Anatomical distribution of opioid receptors in mammalian. // In: Handbook of experimental pharmacology. Opioids. -Herz A. (Ed.). -Springer-Verlag. Berlin. — 1993. — V. 1. — No. 104. — P. 79−105
56. Dhawan B.N., Cesselin F., Raghubir R., Reisine T., Bradley P.B., Portoghese P. S., Hamon M. Internation union of pharmacology. XII. Classification of opioid receptors. // Pharmacol. Rev. 1996. — V. 48. — P. 567−592
57. Palczewski K., Kumasaka T., Hori T., Behnke C.A., Motoshima H., Fox B.A., Le Trong I., Teller D.C., Okada T., Stenkamp R.E., Yamamoto M., Miyano M. Crystal structure of rhodopsin: A G protein-coupled receptor. // Science. 2000. — V. 289. — P. 739−745
58. Fowler C.B., Pogozheva I.D., LeVine III H., Mosberg H.I. Refinement of a
59. Homology Model of the //-Opioid Receptor Using Distance Constraints from Intrinsic and Engineered Zinc-Binding Sites. // Biochemistry. 2004. -V.43.-P. 8700−8710
60. Fowler C.B., Pogozheva I.D., Lomize A.L., LeVine III H., Mosberg H.I. Complex of an Active /?-Opioid Receptor with a Cyclic Peptide Agonist Modeled from Experimental Constraints. // Biochemistry. 2004. — V. 43. -P. 15 796−15 810
61. Bernard D., Coop A., MacKerell A.D., Jr. Quantitative Conformationally Sampled Pharmacophore for S Opioid Ligands: Reevaluation of Hydrophobic Moieties Essential for Biological Activity. // J. Med. Chem. -2007.-V. 50.-P. 1799−1809
62. Aldrich J.V., Vigil-Cruz S.C. Narcotic Analgesics. // In: Burger’s Medicinal
63. Chemistry and Drug Discovery. Abraham D. (Ed.). — John Wiley & Sons. -New York. — 2003. — V. 6. — Chapt. 7. — P. 329−481
64. White J.M., Irvine R.J. Mechanisms of fatal opioid overdose. // Addiction.1999.-V. 94.-P. 961−972
65. Pappagallo M. Incidence, prevalence and management of opioid bowel dysfunction. // Amer. J. Surg. 2001. — V. 182. — P. S11 -S18
66. Chakrabarti S., Wang L., Tang W.J., Gintzler A.R. Chronic morphine augments adenylyl cyclase phosphorylation: Relevance to altered signaling during tolerance/dependence. // Mol. Pharmacol. 1998. — V. 54. — P. 949 953
67. Martin T.J., Eisenach J.C. Pharmacology of opioid and nonopioid analgesicsin chronic pain states. // J. Pharmacol. Exp. Ther. 2001. — V. 299. — P. 811−817
68. Coop A., MacKerell A.D., Jr. The future of opioid analgesics. // Amer. J. Pharm. Educ. 2003. — V. 66. — P. 153−156
69. Portoghese P. S. A new concept on the mode of interaction of narcotic analgesics with receptors. // J. Med. Chem. 1965. — V. 8. — P. 609−616
70. Di Maio J., Ahmed F.R., Schiller P., Belleau B. // In: Recent advances in receptor chemistry. -Gaultieri F., Giannella M., Melchiorre C. (Eds.). -Elsevier/North-Holland. Amsterdam. — 1979. — P. 221
71. Portoghese P. S. The role of concepts in structure-activity relationship studiesof opioid ligands. // J. Med. Chem. 1992. — V. 35. — P. 1927−1937
72. Carroll F.I. 2002 Medicinal chemistry division award address: Monoaminetransporters and opioid receptors. Targets for addiction therapy. // J. Med. Chem. -2003. V. 46.-P. 1775−1794
73. Bond R.A., Bouvier M. Inverse agonists and G-protein-coupled receptors. //
74. Drugs Pharm. Sci. 1998. — V. 89. — P. 363−377
75. Neilan C.L., Akil H., Woods J.H., Traynor J.R. Constitutive activity of thedelta-opioid receptor expresed in C6 glimoa cells: Identification of non-peptide delta-inverse agonists. // Br. J. Pharmacol. 1999. — V. 128. — P. 556−562
76. Erez M., Takemori A.E., Portoghese P. S. Narcotic antagonistic potency ofbivalent ligands which contain A-naltrexamine. Evidence for bridging between proximal recognition sites. // J. Med. Chem. 1982. — V. 25. — P. 847−849
77. Portoghese P. S., Ronsisvalle G., Larsen D.L., Yim C.B., Sayre L.M., Takemori A.E. Opioid agonist and antagonist bivalent ligands as receptor probes. // Life Sci. 1982. — V. 31. — P. 1283−1286
78. Cvejic S., Devi L. Dimerization of the? opioid receptor: Implication for a role in receptor internalization. // J. Biol. Chem. 1997. — V. 272. — P. 26 959−26 964
79. Jordan B.A., Cvejic S., Devi L.A. Opioids and their complicated receptor complexes. // Neuropsychopharmacology. 2000. — V. 23. — P. S5-S18
80. George S.R., Fan T., Xie Z., Tse R., Tamni V., Varghese G., O’Dowd B.F.
81. Oligomerization of and ?-opioid receptors: Generation of novel functional properties. // J. Biol. Chem. 2000. — V. 275. — P. 26 128−26 135
82. Portoghese P. S., Larson D.L., Sayre L.M., Yim C.B., Ronsisvalle G., Tam
83. S.W., Takemori A.E. Opioid agonist and antagonist bivalent ligands. The relationship between spacer length and selectivity at multiple opioid receptors. J. Med. Chem. 1986. -V. 29. — P. 1855−1861
84. Portoghese P. S., Nagase H., Takemori A.E. Only one pharmacophore is required for the ** opioid antagonist selectivity of norbinaltorphimine. // J. Med. Chem. 1988.-V. 31.-P. 1344−1347
85. Portoghese P. S., Ronsisvalle G., Larson D.L., Takemori A.E. Synthesis andopioid antagonist potencies of naltrexamine bivalent ligands with conformationally restricted spacers. // J. Med. Chem. 1986. — V. 29. — P. 1650−1653
86. Daniels J.D., Kulkarni A., Xie Z., Bhushan R.G., Portoghese P. S. A bivalentlignd (KDAN-18) containing^-antagonist and ««-agonist pharmacophores bridges S2 and ^ opioid receptor phenotypes. // J. Med. Chem. 2005. — V. 48. — P. 1713−1716
87. Neumeyer J.L., Zhang A., Xiong W., Gu X.-H., Hilbert J.E., Knapp B.I., Negus S. S., Mello N.K., Bidlack J.M. Design and synthesis of novel dimeric morphinan ligands for k and H opioid receptors. // J. Med. Chem. -2003.-V. 46.-P. 5162−5170
88. Peng X., Knapp B.I., Bidlack J.M., Neumeyer J.L. Synthesis and preliminaryin vitro investigation of bivalent ligands containing homo- and heterodimeric pharmacophores at M, and ** opioid receptors. // J. Med. Chem. 2006. — V. 49. — P. 256−262
89. Mathews J.L., Peng X., Xiong W., Zhang A., Negus S.S., Neumeyer J.L., Bidlack J.M. Characterization of a novel bivalent morphinan possessing k agonist and V agonist/antagonist properties. // J. Pharmacol. Exp. Ther. -2005.-V. 315.-P. 821−827
90. Fulton B.S., Knapp B.L., Bidlack J.M., Neumeyer J.L. Effect of linker substitution on the binding of butorphan univalent and bivalent ligands to opioid receptors. // Bioorg. Med. Chem. Lett. 2010. — V. 20. — P. 15 071 509
91. Peng X., Knapp B.I., Bidlack J.M., Neumeyer J.L. Pharmacological properties of bivalent ligands containing butorphan linked to nalbuphine, naltrexone, and naloxone at M, and opioid receptors. // J. Med. Chem. -2007. V. 50. — P. 2254−2258
92. Brady L.S., Devi L.A. Dimerization of G-protein-coupled receptors: Implications for drug design and signaling. // Neuropsychopharmacology. -2000.-V. 23.-P. S1-S77
93. Devi L.A. Heterodimerization of G-protein-coupled receptors: pharmacology, signaling and trafficking. // Trends Pharmacol. Sci. 2001. -V. 22.-P. 532−537
94. Gomes I., Jordan B.A., Gupta A., Rois C., Trapaidze N., Devi L.A. G-Protein coupled receptor dimerization: implications in modulating receptor function. // J. Mol. Chem. 2001. — V. 79. — P. 226−242
95. Morphy R., Kay C., Rankovic Z. From magic bullets to designed multipleligands. // Drug Discovery Today. 2004. — V. 9. — P. 641−651
96. Owens J. Bridging the GPCR gap. // Nat. Rev. Drug Discovery. 2006. — V.5.-P. 105
97. Dondio G., Ronzoni S., Petrillo P. Non-peptide S opioid agonists and antagonists (Part II). // Expert Opin. Ther. Pat. 1999. — V. 9. — P. 353−374
98. Glass M.J., Billington C.J., Levine A.S. Opioids and food intake: distributedfunctional neural pathways? // Neuropeptides. 1999. — V. 33. — P. 360 368
99. Reneric J.-P., Bouvard M.P. Opioid receptor antagonists in psychiatry: beyond drug addiction. // CNS Drugs. 1998. — V. 10. — P. 365−382
100. Choi Y.S., Billings J.A. Opioid antagonists: a review of their role in palliative care, focusing on use in opioid-related constipation. // J. Pain Symptom Manage. 2002. — V. 24. — P. 71−90
101. Stein C., Schafer M., Machelska H. Attaching pain at its source: new perspectives on opioids. // Nat. Med. 2003. — V. 9. — P. 1003−1008
102. DeHaven-Hudkins D.L., Dolle R.E. Peripherally restricted opioid agonists asnovel analgesic agents. // Curr. Pharm. Des. 2004. — V. 10. — P. 743−757
103. Зайцев C.B., Ярыгин K.H., Варфоломеев С. Д. Наркомания. Нейропептид-морфиновые рецепторы. — М. — Изд-во МГУ. 1993. — 256 с.
104. Barltrop J.A. Syntheses in the morphine series. Part I. Derivatives of bicyclo3: 3: l.-2-azanonane. // J. Chem. Soc. 1947. — P. 399−401
105. Palmer D.C., Strauss M.J. Benzomorphans: synthesis, stereochemistry reactions, and spectroscopic characterizations. // Chem. Rev. 1977. — V. 77.-P. 1−36
106. Bosch J., Bonjoch J. Synthesis of 2-azabicyclo3.3.1.nonanes. // Heterocycles. 1980. -V. 14. — P. 505−529
107. May E.L., Murphy J.G. Structures related to morphine. III. Synthesis of ananalog of iV-methylmorphinan. // J. Org. Chem. 1955. — V. 20. — P. 257 263
108. Grewe R., Mondon A. Synthesen in der Phenantren-Reihe, VI. Mitteil.: Synthese des Morphinans. // Chem. Ber. 1948. — V. 81. — P. 279−286
109. Grewe R., Mondon A., Nolte E. Die Totalsynthese des Tetrahydro-desoxycodeins. // Justus Liebigs Ann. Chem. 1949. — V. 564. — P. 161 198
110. May E.L., Fry E.M. Structures related to morphine. VIII. Further syntheses in the benzomorphan series. // J. Org. Chem. 1957. — V. 22. — P. 13 661 369
111. Meyers A.I., Dickman D.A., Bailey T.R. Asymmetric synthesis of 2-alkyl pyrrolidines and piperidines. Synthesis of (+)-metazocine. // J. Amer. Chem. Soc. 1985. — V. 107. — P. 7974−7978
112. Trost B.M., Tang W. Migratory hydroamination: A facile enantioselective synthesis of benzomorphans. // J. Amer. Chem. Soc. 2003. — V. 125. — P. 8744−8745
113. Saito S., May E.L. Structures related to morphine. XXI. An alternative synthesis of diastereoisomeric 2'-hydroxy-2,5,9-trimethyl-6,7-benzomorphans. //J. Org. Chem. 1962. — V. 27. — P. 1087−1089
114. Chignell C.F., May E.L. Structures related to morphine. XXIX. Further experiments on the stereo-controlled reduction of 9-methylene-6,7-benzomorphans. // J. Med. Chem. 1965. — V. 8. — P. 385−386
115. Fry E.M. Stereospecific tautomerism in a 1,2-dihydropyridine. A P-benzomorphan synthesis. // J. Org. Chem. 1963. — V. 28. — P. 1869−1874
116. Kanematsu K., Takeda M., Jacobson A.E., May E.L. Synthesis of 6,7-benzomorphan and related nonquaternary carbon structures with marked analgetic activity. // J. Med. Chem. 1969. — V. 12. — P. 405−408
117. Stella L. Homolytic cyclizations of iV-chloroalkenylamines. // Angew. Chem. Int. Ed. Engl. 1983. — V. 22. — P. 337−350
118. Stella L., Raynier B., Surzur J.M. Synthesis of 2-methyl-6,7-benzomorphane via radical cyclisation. // Tetrahedron Lett. 1977. — P. 2721−2724
119. Stella L., Raynier B., Surzur J.M. Synthese radicalaire d’analgesiques potentiels: aryl-4 piperidines substituees en 2 et benzomorphanes. // Tetrahedron. 1981. — V. 37. — P. 2843−2854
120. Boger D.L., Patel M., Mullican M.D. Synthetic analgesics: preparation of racemic 6,7-benzomorphans. // Tetrahedron Lett. 1982. — V. 23. — P. 4559−4562
121. Takeda M., May E.L. Acyl derivatives of 5-hydroxy-6,7-benzomorphans. Prodine congeners. // J. Med. Chem. 1970. — V. 13. — P. 1223−1224
122. Walker G.N., Alkalay D. New benzomorphan ring closure in the synthesis of 5-phenylbenzomorphans. // J. Org. Chem. 1966. — V. 31. — P. 19 051 911
123. Gless R.D., Rapoport H. 6,7-Benzomorphans. Stereospecific synthesis of 2,9" — and 2,9/?-dimethyl-2 -methoxy-6,7-benzomorphans. // J. Org. Chem. 1979. — V. 44. — P. 1324−1336
124. Oh-ishi T., Jacobson A.E., Wilson R.S., Yeh H.J.C., May E L. Synthesis of 2,9/?-dimethyl-6,7-benzomorphan. // J. Org. Chem. 1974. — V. 39. — P. 1347−1349
125. Inoue H., May E.L. Synthesis and pharmacology of 2,9a-dimethyl-2'-hydroxy-6,7-benzomorphan. // J. Med. Chem. 1976. — V. 19. — P. 259 262
126. Hodjat H., Lattes A., Laval J.P., Moulines J., Perie J.J. Aminomercuration X Synthese dlieterocycliques monospiranniques par aminomercuration intramoleculaire. // J. Heterocycl. Chem. — 1972. — V. 9. — P. 1081−1086
127. Lattes A., Perie J.J. Aminomercuration reaction principle and preliminary results // C. R. Acad. Sci. — 1966. -V. 262. -P. 1591−1594
128. Kitamura M., Hsiao Y., Noyori R., Takaya H. General asymmetric synthesis of benzomorphans and morphinans via enantioselective hydrogenation // Tetrahedron Lett. 1987. — V. 28. — P. 4829−4832
129. Mitsuhashi K., Shiotani S., Oh-uchi R., Shiraki K. Syntheses of azabenzobicycloalkanes. // Chem. Pharm. Bull. 1969. — V. 17. — P. 434 453
130. Pat. 3 539 637 US. N-Carbamoyl- and TV-thiocarbamoyl-2,3,4,5-tetrahydro-l, 4-methano-li/-3-benzazepines. / Clarke F.H., Block F.B. Publ. 10.11.1970 — (Chem. Abstr. — 1971. — V. 74 — No. 99 911 k)
131. Kometani T., Shiotani S. Synthesis and analgetic activity of some benzomorphan analogues. // J. Med. Chem. 1978. — V. 21. — P. 11 051 110
132. Shiotani S., Kometani T., Mitsuhashi K. 2,3,4,5,6,7-Hexahydro-l, 6-methano- l//-3-benzazonine derivatives as analgesics. // J. Med. Chem. -1975.-V. 18.-P. 1266−1267
133. Finch H. Facile synthesis of 1-substituted C-norbenzomorphans. // Tetrahedron Lett. 1982. — V. 23. — P. 4393−4396
134. Takeda M., Kugita H. Homologs of benzomorphan derivatives. 1. // J. Med. Chem. 1970. -V. 13. — P. 630−634
135. Takeda M., Inoue H., Konda M., Saito S., Kugita H. An improved synthesis of a 9-oxo-6,7-benzomorphan and its homolog. A novel rearrangement of heterocyclic enamines via bromination. // J. Org. Chem. -1972. V. 37. — P. 2679 (1972)
136. Shiotani S., Kometani T., Mitsuhashi K. Studies on structure-activity relationship of analgetics. XIII. Syntheses of homobenzomorphans and related compounds. (1). // Chem. Pharm. Bull. 1972. — V. 20. — P. 277 283
137. Shiotani S., Kometani T. Studies on structure-activity relationship of analgetics. XVII. Syntheses of homobenzomorphans and related compounds. (2). // Chem. Pharm. Bull. 1973. — V. 21. — P. 1053−1060
138. Archer S., Albertson N.F., Harris L.S., Pierson A.K., Bird J.G. Pentazocine. Strong analgesics and analgesic antagonists in the benzomorphan series. // J. Med. Chem. 1964. — V. 7. — P. 123−127
139. Wentland M.P., Ye Y., Cioffi C.L., Lou R., Zhou Q., Xu G., Duan W., Dehnhardt C.M., Sun X., Cohen D.J., Bidlack J.M. Syntheses and opioid receptor binding affinities of 8-amino-2,6-methano-3-benzazocines. // J. Med. Chem. 2003. — V. 46. — P. 838−849
140. Wentland M.P., Xu G., Cioffi C.L., Ye Y., Duan W., Cohen D.J., Colasurdo A.M., Bidlack J.M. 8-Aminocyclazocine analogues: synthesis and structure-activity relationships. // Bioorg. Med. Chem. Lett. 2000. -V. 10.-P. 183−187
141. Wentland M.P., Lou R., Ye Y., Cohen D.J., Richardson G.P., Bidlack J.M. 8-Carboxamidocyclazocine analogues: redefining the structure-activity relationships of 2,6-methano-3-benzazocines. // Bioorg. Med. Chem. Lett. -2001. -V. 11. P. 623−626
142. Grewe R. Das Problem der Morphin-Synthese. // Naturwissenschaften. -1946.-V. 33.-P. 333−336
143. Grewe R. Synthetische Arzneimittel mit Morphin-Wirkung. // Angew. Chem. 1947. — V. 59. — P. 194−199
144. Ginos J.Z. Precursors to apomorphine and morphinan analogs. Catalytic reduction of quinoline and isoquinoline // J. Org. Chem. 1975. — V. 40. -P. 1191−1195
145. Pat. 3 634 429 US. Morphinan derivatives and preparation thereof. / Leimgruber W., Mohacsi E. Publ. 11.01.1972
146. Fry E.M., May E.L. The Stevens rearrangement in the benzomorphan synthesis. // J. Org. Chem. 1961. — V. 26. — P. 2592−2594
147. Grewe R., Friedrichsen W. Die Cyclisierung von Octahydro-isochinolinderivaten durch Morphinan-Ringschlu?. Synthese des Dihydrothebainons. // Chem. Ber. 1967. — V. 100. — P. 1550−1558
148. Morrison G.C., Waite R.O., Shavel J., Jr. An alternate route in the synthesisof morphine. // Tetrahedron Lett. 1967. — P. 4055−4056
149. Beyerman H.C., Buurman E., Maat L. A high yield synthesis of Af-formyl-1-methylnordihydrothebainone. // J. Chem. Soc., Chem. Commun. 1972. -P. 918
150. Beyerman H.C., Lie T.S., Maat L., Bosman H.H., Buurman E., Bijsterveld E.J.M., Sinnige H.J.M. A convenient synthesis of codeine and morphine. // Reel. Trav. Chim. Pay-Bas. 1976. — V. 95. — P. 24−25
151. Schnider O., Hellerbach J. Synthese von Morphinanen. (2. Mitteilung). // Helv. Chim. Acta. 1950. -V. 33. — P. 1437−1448
152. Grewe R., Hamann R., Jacobsen G., Nolte E., Riecke K. Die Darstellung von Oktahydro-isochinolin-Derivaten durch Ringschlu?. // J. Liebigs Ann. Chem.- 1953.-V. 581.-P. 85−116
153. Henecka H. Neue Synthesen in der Morphinanreiche. // J. Liebigs Ann. Chem. 1953.-V. 583.-P. 110−128
154. Sasamoto M. Synthesis in the morphinan group. V.: Grewe cyclization of d- and /-l-(3,4-ethylenedioxybenzyl)-2-methyl-l, 2,3,4,5,6,7,8-octahydroisoquinoline. // Chem. Pharm. Bull. 1960. — V. 8. — P. 980−988
155. Schnider O., Brossi A., Vogler K. Oxy-morphinane. 5. Mitteilung. Optisch aktive Benzyl-octahydro-isochinoline // Helv. Chim. Acta. 1954. — V. 37. -P. 710−720
156. Schnider O., Griissner A. Oxy-morphinane. (3. Mitteilung). Optisch aktive 3-Oxy-morphinane. // Helv. Chim. Acta. 1951. — V. 34. — P. 2211−2217
157. Hellerbach J., Griissner A., Schnider O. Hydroxy-morphinane. 7. Mitteilung. (-)-3-Hydroxy-N-allyl-morphinan und verwandte Verbindungen. // Helv. Chim. Acta. 1956. — V. 39. — P. 429−440
158. Gates M., Montzka T.A. Some potent morphine antagonists possessing high analgesic activity. // J. Med. Chem. 1964. — V. 7. — P. 127−131
159. Gates M. //Adv. Biochem. Psychopharmacol. 1974. — P. 8. — P. 51−58
160. Sawa Y.K., Kawaski K., Mayeda S. Studies on morphinan derivatives. I.: By-products in the synthesis of 3-methoxy-N-methylmorphinan. // Chem. Pharm. Bull. 1960. — V. 8. — P. 960−966
161. Monkovic I., Conway T.T., Wong H., Perron Y.G., Pachter I.J., Belleau B. Total synthesis and pharmacological activities of TV-substituted 3,14-dihydroxymorphinans. I. // J. Amer. Chem. Soc. 1973. — V. 95. — P. 79 107 912
162. Monkovic I., Wong H., Pircio A.W., Perron Y.G., Pachter I.J., Belleau B. Oxilorphan and butorphanol. Potent narcotic antagonists and nonaddicting521analgesics in the 3,14-dihydroxymorphinan series. Part V. // Can. J. Chem.- 1975. -V. 53. P. 3094−3102
163. Monkovic I., Wong H. Synthetic morphinans and hasubanans. VI. Total synthesis of 3-hydroxyisomorphinans, 3-hydroxyhasubanans, and 3,9-dihydroxyhasubanans. // Can. J. Chem. 1976. — V. 54. — P. 883−891
164. Monkovic I., Bachand C., Wong H. A stereoselective total synthesis of 14-hydroxymorphinans. Grewe approach. // J. Amer. Chem. Soc. 1978. — V. 100.-P. 4609−4610
165. Barton D.H.R., Bhakuni D.S., James R., Kirby G.W. Phenol oxidation and biosynthesis. Part XII. Stereochemical studies related to the biosynthesis of the morphine alkaloids. // J. Chem. Soc. C. 1967. — P. 128−132
166. Franck B., Teetz V. Model reactions for the biosynthesis of erythrina alkaloids. // Angew. Chem. Int. Ed. Engl. 1971. — V. 10. — P. 411−412
167. Miller L.L., Stermitz F.R., Falck J.R. Electrooxidative cyclization of laudanosine. Novel nonphenolic coupling reaction. // J. Amer. Chem. Soc.- 1971.-V. 93.-P. 5941−5942
168. Maeda S., Ohsugi E. Study on the synthesis of rac-3-methoxy-6-oxo-iV-methylmorphinan. // Chem. Pharm. Bull. 1968. — V. 16. — P. 897−908
169. Olieman C., Nagelhout P., de Groot A.D., Maat L., Beyerman H.C. Synthesis of racemic 3 -hydroxy-N-methy 1−6-oxomorphinan (Chemistry of opium-alkaloids. 14.) // Reel. Trav. Chim. Pays-Bas. 1980. — V. 99. — P. 353−355
170. Brossi A., Hsu F.-L., Rice K.C. A simplified synthesis of (±)-4-hydroxy-./V-methylmorphinan-6-one. //J. Org. Chem. 1982. -V. 47. — P. 5214−5216
171. Hsu F.-L., Rice K.C., Brossi A. Total synthesis of (±)-3-deoxy-7,8-dihydromorphine. Preliminary communication. // Helv. Chim. Acta. -1980. V. 63. — P. 2042−2045
172. Hsu F.-L., Jacobson A.E., Rice K.C., Brossi A. Partial synthesis of 3-deoxydihydromorphine from (-)-4-hydroxy-6-keto-A^-methylmorphinan. // Heterocycles. 1979. — V. 13. — P. 259−261
173. Rozwadowska M.D., Hsu F.-L., Jacobson A.E., Rice K.C., Brossi A. (-)-4-Hydroxy-iV-formylmorphinan-6-one, a versatile intermediate for the synthesis of 3-deoxyopioids. // Can. J. Chem. 1980. — V. 58. — P. 18 551 859
174. Manmade A., Dalzell H.C., Howes J.F., Razdan R.K. (-)-4-Hydroxymorphinanones: their synthesis and analgesic activity. // J. Med. Chem.-1981.-V. 24.-P. 1437−1440
175. Mouralova J., Hajicek J., Trojanek J. On alkaloids. XLV. Partial synthesis of (—)-butorphanol. // Ceskoslov. Farm. 1983. — V. 32. — P. 23−26
176. Sawa Y.K., Horiuchi M., Tanaka K. Elimination of the 4-hydroxyl group of the alkaloids related to morphine VIII: Synthesis of (-)-3-methoxy-iV-methyl-isomorphinan derivatives. // Tetrahedron. — 1965. — V. 21. — P. 1133−1139
177. Sawa Y.K., Maeda S. Elimination of the 4-hydroxyl group of the alkaloids related to morphine. III. // Tetrahedron. 1964. — V. 20. — P. 2247−2253
178. Sawa Y.K., Tsuji N., Maeda S. Elimination of the 4-hydroxyl group of the alkaloids related to morphine IV. // Tetrahedron. — 1964. — V. 20. — P. 2255−2258
179. Schopf C., Pfeifer T. Teilsynthesen in der Morphinreiche: I. Der Ubergangaus der Dihydrothebainon- in die Dihydrokodeinon-Reihe. // J. Liebigs Ann. Chem. 1930. — V. 483. — P. 157−169
180. Mannich C., Lowenheim H. Ueber zwei neue Reduktionsprodukte des Kodeins. // Arch. Pharm. 1920. — V. 258. — P. 295−316
181. Schopf C., Hirsch H. Die Darstellung des wahren Thebainons und die Einwirkung von konz. Salzsaure auf Thebain. (II. Mitteilung uber die Saureumlagerungen der Morphiumalkaloide). // J. Liebigs Ann. Chem. -1931. V. 489.-P. 224−251
182. Perrine T.D., Small L.F. Reactions of dihydrocodeinone with hydrazine and with ethyl mercaptan. // J. Org. Chem. 1952. — V. 17. — P. 1540−1544
183. Rearick D.E., Gates M. A new degradation of thebaine to morphinandienone derivatives. // Tetrahedron Lett. 1970. — V. 11 — P. 507−508
184. Bjeldanes L.F., Rapoport H. Bisulfite mediated oxidation of thebaine. Formation of 6-O-demethylsalutaridine. // J. Org. Chem. 1972. — V. 37. -P. 1453−1454
185. Bentley K.W., Robinson R., Wain A.E. The reduction of thebaine and dihydrothebaine by sodium and ammonia. // J. Chem. Soc. 1952. — P. 958−966
186. Birch A.J., Fitton H. The preparation and some reactions of the irontricarbonyl complex of thebaine. // Austral. J. Chem. 1969. — V. 22. -P. 971−976
187. Razdan R.K., Portlock D.E., Dalzell H.C., Malmberg C. Synthesis of ?-dihydrothebaine. // J. Org. Chem. 1978. — V. 43. — P. 3604−3606
188. Greiner E., Schottenberger H., Wurst K., Schmidhammer H. Novel class of morphinans with acrylonitrile incorporated substructures as key intermediates for non-oxygen-bridged opioid ligands. // J. Amer. Chem. Soc.-2001.-V. 123.-P. 3840−3841
189. Schutz J., Schmidhammer H., Wurst K. Crystal structure of 14/?-hydroxy-3,4-dimethoxy-5#17-dimethylmorphinan-6-one, C20H27N04. // Z. Kristallogr. NCS. 2003. — V. 218. — P. 181 -183
190. Leland D.L., Polazzi J.P., Kotick M.P. Analgesic narcotic antagonists. 3. Preparation of 7D -methyldihydrothebaine-^. // J. Org. Chem. 1980. — V. 45.-P. 4026−4028
191. Kobylecki R.J., Carling R.W., Lord J.A.H., Smith C.F.C., Lane A.C. Common anionic receptor site hypothesis: its relevance to the action of naloxone. // J. Med. Chem. 1982. — V. 25. — P. 116−120
192. Spetea M., Greiner E., Aceto M.D., Harris L.S., Coop A., Schmidhammer H. Effect of a 6-cyano substituent in 14-oxygenated vV-methylmorphinans on opioid receptor binding and antinociceptive potency. // J. Med. Chem. -2005. V. 48. — P. 5052−5055
193. Zhang A., Xiong W., Hilbert J.E., De Vita E.K., Bidlack J.M., Neumeyer J.L. 2-Aminothiazole-derived opioids. Bioisosteric replacement of phenols. // J. Med. Chem. 2004. — V. 47. — P. 1886−1888
194. Coop A., Rothman R.B., Dersch C., Partilla J., Porreca F., Devis P., Jacobson A.E., Rice K.C. ?Opioid affinity and selectivity of 4-hydroxy-3-methoxyindolomorphinan analogues related to naltrindole. // J. Med. Chem. 1999. — V. 42. — P. 1673−1679
195. Kubota H., Rothman R.B., Dersch C., McCullough K., Pinto J., Rice K.C. Synthesis and biological activity of 3-substituted 3-desoxynaltrindole derivatives. // Bioorg. Med. Chem. Lett. 1998. — V. 8. — P. 799−804
196. Coop A., Rice K.C. Direct and simple conversion of codeine to thebainone-A and dihydrothebainone. // Heterocycles. 1999. — V. 50. — P. 39−42
197. Zhang A., Li F., Ding C., Yao Q., Knapp B.I., Bidlack J.M., Neumeyer J.L. Synthesis and pharmacological evaluation of 6,7-indolo/thiazolo-morphinans. Further SAR of levorphanol. // J. Med. Chem. 2007. — V. 50. -P. 2747−2751
198. Olofson R.A., Marts J.T., Senet J.-P., Piteau M., Malfroot T. A new reagent for the selective, high yield 7V-dealkylation of tertiary amines: Improved synthesis of naltrexone and nalbuphine. // J. Org. Chem. 1984. — V. 49. -P. 2081−2082
199. Andrade C.K.Z., Rocha R.O., Vercillo O.E., Silva W.A., Matos R.A.F. DCC/DMAP-mediated coupling of carboxylic acids with oxazolidinones and thiazolidinethiones. // Synlett. 2003. — V. 15. — P. 2351−2352
200. Zhang A., Vliet A.V., Neumeyer J.L. Synthesis of aminothiazole derived morphinans. // Tetrahedron Lett. 2003. — V. 44. — P. 6459−6462
201. Schnider O., Grussner A. Synthese von Oxy-morphinanen. // Helv. Chim. Acta. 1949. — V. 32. — P. 821−828
202. Negus S.S., Mello N.K., Portoghese P. S., Lin C.-E. Effects of kappa opioids on cocaine self-administration by rhesus monkeys. // J. Pharmacol. Exp. Ther. 1997. — V. 282. — P. 44−55
203. Mello N.K., Negus S.S. Effects of kappa opioids agonists on schedule-controlled behavior and cocaine self-administration by rhesus monkeys. // J. Pharmacol. Exp. Ther. 1998. -V. 286. — P. 812−824
204. Bowen C.A., Negus S.S., Zong R., Neumeyer J.L. Bidlack J.M., Mello N.K. Effects of mixed-action kappa/mu opioids on cocaine self-administration and cocaine discrimination by rhesus monkeys. // Neuropsychopharmacology. 2003. — V. 28. — P. 1125−1139
205. Archer S., Glick S.D., Bidlack J.M. Cyclazocine revisited. // Neurochem. Res. 1996. — V. 21. — P. 1369−1373
206. Gates M., Tschudi G. The synthesis of racemic /?-A6-dihydrodesoxycodeine methyl ether. // J. Amer. Chem. Soc. 1950. — V. 72. — P. 4839−4840
207. Gates M., Tschudi G. The synthesis of morphine. // J. Amer. Chem. Soc. -1952.-V. 74.-P. 1109−1110
208. Gates M., Tschudi G. The synthesis of morphine. // J. Amer. Chem. Soc. -1956.-V. 78.-P. 1380−1393
209. Elad D., Ginsburg D. The synthesis of morphine. // J. Amer. Chem. Soc. -1954.-V. 78.-P. 312−313
210. Elad D., Ginsburg D. Syntheses in the morphine series. Part VI. The synthesis of morphine. // J. Chem. Soc. 1954. — P. 3052−3056
211. Weller D.D., Rapoport H. A practical synthesis of codeine from dihydrothebainone. // J. Med. Chem. 1976. — V. 19. — P. 1171−1175
212. DeGraw J.I., Christensen J.C., Brown V.H., Cory M.J. Investigation of the Grewe codeine method. Attempts to achieve a practical synthesis. // J. Heterocycl. Chem. 1974. — V. 11. — P. 363−367
213. Schwartz M.A., Mami I.S. A biogenetically patterned synthesis of the morphine alkaloids. // J. Amer. Chem. Soc. 1975. -V. 97. — P. 1239−1240
214. Knorr L., Horlein H. Zur Kenntniss des Morphins. VII. Mittheilung: Ueberfuhrung des Thebains in Codeinon und Codein. // Ber. 1906. — V. 39.-P. 1409−1414
215. Conroy H. Neopinone. // J. Amer. Chem. Soc. 1955. — V. 77. — P. 59 605 966
216. Gates M. The conversion of codeinone to codeine. // J. Amer. Chem. Soc. -1953.-V. 75.-P. 4340−4341
217. Rapoport H., Lovell C.H., Tolbert B.M. The preparation of morphine-N-methyl-C14. //J. Amer. Chem. Soc. 1951. -V. 73. — P. 5900
218. Lie T.S., Maat L., Beyerman H.C. Synthesis of racemic and chiral codeine and morphine via the dihydrothebainones. (Chemistry of opium alkaloids, Part XI.) // Reel. Trav. Chim. Pays-Bas. 1979. — V. 98. — P. 419−420
219. Musliner W.J., Gates J.W. The replacement of phenolic hydroxyl groups by hydrogen. // J. Amer. Chem. Soc. 1966. — V. 88. — P. 4271−4 273 528
220. Musliner W.J., Gates J.W., Jr. Dehydroxylation of phenols- hydrogenolysis of phenolic ethers: biphenyl. // Org. Synth. 1971. — V. 51. -P. 82−85
221. Rice K.C., Brossi A. Expedient synthesis of racemic and optically active N-norreticuline and TV-substituted and 6-bromo-N-norreticulines. // J. Org. Chem. 1980. — V. 45. — P. 592−601
222. Iijima I., Rice K.C., Silverton J.V. Studies in the (+)-morphinan series I. An alternative conversion of (+)-dihydrocodeinone into (+)-codeine. // Heterocycles. 1977. — V. 6. — P. 1157−1165
223. Rice K.C. A rapid, high-yield conversion of codeine to morphine. // J. Med. Chem. 1977. — V. 20. — P. 164−165
224. Hong C.Y., Kado N., Overman L.E. Asymmetric synthesis of either enantiomer of opium alkaloids and morphinans. Total synthesis of (-) — and (+)-dihydrocodeinone and (-) — and (+)-morphine. // J. Amer. Chem. Soc. -1993.-V. 115.-P. 11 028−11 029
225. White J.D., Hrncier P. Anomalous products from intramolecular C~H insertion by a rhodium carbenoid. Possible involvement of a zwitterionic mechanism. // J. Org. Chem. 1999. — V. 64. — P. 7271−7273
226. Yamada O., Ogasawara K. Diastereoselective synthesis of 3,4-dimethoxy-7-morphinanone: A potential route to morphine. // Org. Lett. 2000. — V. 2. -P. 2785−2788
227. Trost B.M., Toste F.D. Enantioselective total synthesis of (-)-galanthamine. // J. Amer. Chem. Soc. 2000. — V. 122. — P. 11 262−11 263
228. Nagata H., Miyazawa N., Ogasawara K. A concise route to (-)-morphine. // Chem. Commun.-2001.-P. 1094−1095
229. Taber D.F., Neubert T.D., Rheingold A.L. Synthesis of (-)-morphine. // J. Amer. Chem. Soc.-2002. V. 124.-P. 12 416−12 417
230. Trost B.M., Tang W. An efficient enantioselective synthesis of (-)-galanthamine. // Angew. Chem., Int. Ed. 2002. — V. 41. — P. 2795−2797
231. Hudlicky T., Butora G., Feamley S.P., Gum A.G., Stabile M.R. A historical perspective of morphine synthesis. // In: Natural products chemistry. -Atta-ur-Rahman (Ed.). Elsevier. — Amsterdam. — 1996. — V. 18. — P. 45
232. Novak B.H., Hudlicky T., Reed J.W., Mulzer J., Trauner D. Morphine synthesis and biosynthesis. An update. // Curr. Org. Chem. — 2000. — V. 4. -P. 343−362
233. Blakemore P.R., White J.D. Morphine, the proteus of organic molecules. // Chem. Commun. 2002. — P. 1159−1168
234. Taber D.F., Neubert T.D., Schlecht M.F. The enantioselective synthesis of morphine. // In: Strategies and tactics in organic synthesis. -Harmata M. (Ed.). Elsevier. — London. — 2004. — V. 5. — P. 353
235. Zezula J., Hudlicky T. Recent progress in the synthesis of morphine alkaloids. // Synlett. 2005. — V. 3. — P. 388−405
236. Mascavage L.M., Wilson M.L., Dalton D.R. Syntheses of morphine and codeine (1992−2002): Templates for exploration of synthetic tools. // Curr. Org. Synth. 2006. — V. 3. — P. 99−120
237. Mackay M., Hodgkin D.C. A crystallographic examination of the structure of morphine. // J. Chem. Soc. 1955. — P. 3261−3267
238. Kartha G., Ahmed F.R., Barnes W.H. Refinement of the crystal structure of codeine hydrobromide dihydrate, and establishment of the absolute configuration of the codeine molecule. // Acta Cryst. 1962. — V. 15. — P. 326−333
239. Bryant R.J. The manufacture of medicinal alkaloids from the opium poppy a review of a traditional biotechnology. // Chem. Ind. — 1988. — V. 5. — P. 146−153
240. Кунах B.A., Кацан B.A. Биосинтез изохинолиновых алкалоидов мака в природе и в культуре in vitro. 2. Мак прицветниковый {Papaver bracteatum Lindl.) // Укр. 6ioxiM. журн. 2004. — Т. 76. — С. 29−44
241. Fairbairn J.W., Helliwell К. Papaver bracteatum Lindley: thebaine content in relation to plant development. // J. Pharm. Pharmacol. 1977. — V. 29. -P. 65−69
242. Коновалова P. А., Киселев B.B. Об алкалоидах семейства Papaveraceae. IX. О строении орипавина. // Ж. общей химии. 1948. -Т. 18.-С. 855−858
243. Pat. 2 778 832 US. Reduction of codeinone to codeine. / Gates M.D., Jr. -Publ. 22.01.1957
244. Barber R.B., Rapoport H. Conversion of thebaine to codeine. // J. Med. Chem. 1976.-V. 19.-P. 1175−1180
245. Pat. 3 112 323 US. Method for the preparation of codeinone from thebaine. / Krausz F. Publ. 1963
246. Gavard J.-P., Krausz F., Rull T. Sur une nouvelle methode de preparation de la codeinone a partir de la thebaine. // Bull. Soc. Chim. Fr. 1965. — P. 486−490
247. Lawson J.A., DeGraw J.I. An improved method for O-demethylation of codeine. // J. Med. Chem. 1977. — V. 20. — P. 165−166
248. Gordon M. Abuse of CNS agents. // Annu. Rep. Med. Chem. 1974. — V. 9.-P. 38−49
249. Iijima I., Minamikawa J., Jacobson A.E., Brossi A., Rice K.C. Studies in the (+)-morphinan series. 4. A markedly improved synthesis of (+)-morphine. // J. Org. Chem. 1978. — V. 43. — P. 1462−1463
250. Balboni G., Salvadori S., Marczak E.D., Knapp B.I., Bidlack J.M., Lazarus L.H., Peng X., Si Y.G., Neumeyer J.L. Opioid bifunctional ligands from morphine and the opioid pharmacophore Dmt-Tic. // Eur. J. Med. Chem. -2011.-V. 46.-P. 799−803
251. Yeh H.J.C., Wilson R.S., Klee W.A., Jacobson A.E. and halomorphides: stereochemistry, analgesic potency, toxicity, and interaction with narcotic receptors in vitro II J. Pharm. Sci. 1976. — V. 65. — P. 902 904
252. Kotick M.P., Leland D.L., Polazzi J.O., Schut R.N. Analgesic narcotic antagonists. 1. 8/?-Alkyl-, 8/?-acyl-, and 8/?-(tertiary alcohol) dihydrocodeinones and -dihydromorphinones. // J. Med. Chem. -1980.-V. 23.-P. 166−174
253. Reden J., Reich M.F., Rice K.C., Jacobson A.E., Brossi A., Streaty R.A., Klee W.A. Deoxymorphines: role of the phenolic hydroxyl in antinociception and opiate receptor interactions. // J. Med. Chem. 1979. -V. 22.-P. 256−259
254. Csutoras C., Zhang A., Bidlackb J.M., Neumeyer J.L. An investigation of the TV-demethylation of 3-deoxymorphine and the affinity of the alkylation products to M-, 5, and k receptors. // Bioorg. Med. Chem. 2004. — V. 12. -P. 2687−2690
255. Hedberg M.H., Johansson A.M., Fowler C.J., Terenius L., Hacksell U. Palladium-catalyzed synthesis of C3-substituted 3-deoxymorphines. // Bioorg. Med. Chem. Lett. 1994. — V. 4. — P. 2527−2532
256. Crooks P.A., Kottayil S.G., Al-Ghananeem A.M., Byrn S.R., Butterfield D.A. Opiate receptor binding properties of morphine-, dihydromorphine-, and codeine 6-O-sulfate ester congeners. // Bioorg. Med. Chem. Lett. -2006.-V. 16.-P. 4291−4295
257. Paul D., Standifer K.M., Inturrisi C.E., Pasternak G.W. Pharmacological characterization of morphine-6 beta-glucuronide, a very potent morphine metabolite. // J. Pharmacol. Exp. Ther. 1989. — V. 251. — P. 477−483
258. MacDougall J.M., Zhang X.-D., Polgar W.E., Khroyan T.V., Toll L., Cashman J. R. Design, chemical synthesis, and biological evaluation of thiosaccharide analogues of morphine- and codeine-6-glucuronide. // J. Med. Chem. 2004. — V. 47. — P. 5809−5815
259. MacDougall J.M., Zhang X.-D., Polgar W.E., Khroyan T.V., Toll L., Cashman J.R. Synthesis and in vitro biological evaluation of a carbon glycoside analogue of morphine-6-glucuronide // Bioorg. Med. Chem. Lett. -2005.-V. 15.-P. 1583−1586
260. Weijlard J., Erickson A.E. 7V-Allylnormorphine. // J. Amer. Chem. Soc. -1942.-V. 64.-P. 869−870 266. von Braun J. Die Aufspaltung cyclischer Basen durch Bromcyan. // Chem. Ber. 1909. — V. 42. — P. 2035−2057
261. Hageman H.A. The von Braun cyanogen bromide reaction. // Org. React. -1953.-V. 7.-P. 198−262
262. Polazzi J.O., Schut R.N., Kotick M.P., Howes J.F., Osgood P.F., Razdan R.K., Villarreal J.E. Analgesic narcotic antagonists. 2. 8-Alkylmorphinan-6-ones. // J. Med. Chem. 1980. — V. 23. — P. 174−179
263. Leland D.L., Kotick M.P. Analgesie narcotic antagonists. 4. 7-Methyl-N-(cycloalkylmethyl)-3-hydroxy morphinan-6-one and -isomorphinan-6-one. // J. Med. Chem. 1980. — V. 23. — P. 1427−1431
264. Hosztafi S., Makleit S., Bognar R. iV-Demethylation of morphine alkaloids. Preparation of norneopine // Acta Chim. Acad. Sei. Hung. 1980. — V. 103. -P. 371−375
265. McCamley K., Ripper J.A., Singer R.D., Scammells P.J. Efficient N-demethylation of opiate alkaloids using a modified nonclassical Polonovski reaction. // J. Org. Chem. 2003. — V. 68. — P. 9847−9850
266. Kenner G.W., Stedman R.J. The compounds of alkylamines with esters of azodicarboxylic acid. // J. Chem. Soc. 1952. — P. 2089−2094
267. Huisgen R., Jakob F. Additionsreaktionen der NN-Doppelbindung II Der Chemismus einiger weiterer Reaktionen des Azodicarbonesters. // J. Liebigs Ann. Chem. 1954. — V. 590. — P. 37−54
268. Pat. 3 342 824 US. Normorphines. / Pohland A., Sullivan H.R. Publ. 19.09.1967
269. Merz H., Pook K.-H. Reaktionen des Thebains mit Azodicarbonsaureestern. // Tetrahedron. 1970. — V. 26. — P. 1727−1741
270. Campbell J.A. Cleavage of trialkylamines by chloroformates. // J. Org. Chem. 1957. — V. 22. — P. 1259−1260
271. Kraiss G., Nador K. A convenient synthesis of nortropine from tropine or tropinone. // Tetrahedron Lett. 1971. — V. 12. — P. 57−58
272. Abdel-Monem M.M., Portoghese P. S. TV-Demethylation of morphine and structurally related compounds with chloroformate esters. // J. Med. Chem. 1972.-V. 15.-P. 208−210
273. Hobson J.D., McCluskey J.G. Cleavage of tertiary bases with phenyl chloroformate: the reconversion of 21-deoxyajmaline into ajmaline. // J. Chem. Soc.-1967.-P. 2015−2 017 535
274. Rice K.C., May E.L. Procedural refinements in the Af-demethylation of morphine and codeine using phenyl chloroformate and hydrazine. // J. Heterocycl. Chem. 1977. — V. 14. — P. 665−666
275. Rice K.C. An improved procedure for the 7V-demethylation of 6,7-benzomorphans, morphine, and codeine. // J. Org. Chem. 1975. — V. 40. -P. 1850−1851
276. Brine G.A., Boldt K.G., Hart C.K., Carroll F.I. The N-demethylation of morphine and codeine using methyl chloroformate. // Org. Prep. Proced. Int. 1976. — V. 8. — P. 103−106
277. Gao Y., Traino T.M., Vouros P., Neumeyer J.L. The synthesis of multiple deuterated iV-n-propyl-norapomorphine N-(d7) and derivatives. // J. Labelled Compd. Radiopharm. 1988. — V. 25. — P. 293−299
278. Olofson R.A., Pepe J.P. An efficient synthesis of N-cyclobutylmethylnoroxymorphone from thebaine. // Tetrahedron Lett. -1977.-V. 18.-P. 1575−1578
279. Montzka T.A., Matiskella J.D., Partyka R.A. 2,2,2-Trichloroethyl chloroformate: A general reagent for demethylation of tertiary methylamines. // Tetrahedron Lett. 1974. — V. 15. — P. 1325−1327
280. Pat. 71 29 153 JP. B/C trans 3,6n-Dihydroxy-4,5-epoxy-A^-methyl morphinan-7-ene. / Takeda M., Kugita K. Publ. 24.08.1971 — Chem. Abstr. — 1971. -V. 75.-No. 14 1030v
281. Inoue H., Takeda M., Kugita H. Synthesis of B/C trans-fused morphine structures. IV. Synthesis of B/C ?rara-isomorphine. // Chem. Pharm. Bull. -1970.-V. 18.-P. 1569−1575
282. Leland D.L., Kotick M.P. Analgesic narcotic antagonists. 5. 7,7-Dimethyldihydrocodeinones and 7,7-dimethyldihydromorphinones. // J. Med. Chem. 1981. — V. 24. — P. 717−721
283. Kotick M.P., Leland D.L., Polazzi J.O., Howes J.F., Bousquet A.R. Analgesic narcotic antagonists. 8. 7"-Alkyl-4,5"-epoxymorphinan-6-ones. // J. Med. Chem. 1981. — V. 24. — P. 1445−1450
284. Kopcho J.J., Schaeffer J.C. Selective O-demethylation of 7"-(aminomethyl)-6,14-e"fifo-ethenotetrahydrothebaine. // J. Org. Chem. -1986.-V. 51.-P. 1620−1622
285. Pat. 1 136 214 GB. Thebaine and oripavine derivatives. / Bentley K.W. -Publ. 11.12.1968. Chem. Abstr. — 1966. — V. 70. — No. 78218s
286. Weissman S.A., Zewge D. Recent advances in ether dealkylation. // Tetrahedron. 2005. — V. 61. — P. 7833−7863
287. Bhatt M.V., Kulkarni S.U. Cleavage of ethers. // Synthesis. 1983. — P. 249−282
288. Kok G.B., Pye C.C., Singer R.D., Scammells P.J. Two-step iron (0)-mediated iV-demethylation of TV-methyl alkaloids. // J. Org. Chem. 2010. -V. 75.-P. 4806−4811
289. Dong Z., Scammells P.J. New methodology for the 7V-demethylation of opiate alkaloids. // J. Org. Chem. 2007. — V. 72. — P. 9881−9885
290. Kok G., Ashton T.D., Scammells P.J. An improved process for the N-demethylation of opiate alkaloids using an iron (II) catalyst in acetate buffer. // Adv. Synth. Catal. 2009. — V. 351. — P. 283−286
291. Zewge D., King A., Weissman S., Tschaen D. Enhanced O-dealkylation activity of SiCl4/LiI with catalytic amount of BF3. // Tetrahedron Lett. -2004. V. 45. — P. 3729−3732
292. Thomas R.M., Reddy G.S., Iyengar D.S. An efficient and selective deprotection of allyl ethers by a CeCl3 7H20-NaI system. // Tetrahedron Lett. 1999. — V. 40. — P. 7293−7294
293. Maeyama K., Kobayashi M., Yonezawa N. Nickel/zinc-mediated alkyl carbon-oxygen bond cleavage of alkyl aryl ethers. // Synth. Commun. -2001.-V. 31.-P. 869−875
294. Boovanahalli S.K., Kim D.W., Chi D.Y. Application of ionic liquid halide nucleophilicity for the cleavage of ethers: A green protocol for the regeneration of phenols from ethers. // J. Org. Chem. 2004. — V. 69. — P. 3340−3344
295. Oussai’d A., Thach L.N., Loupy A. Selective dealkylations of alkyl aryl ethers in heterogeneous basic media under microwave irradiation. // Tetrahedron Lett. 1997. -V. 38. — P. 2451−2454
296. Kulkarni P.P., KadamA.J., ManeR.B., Desai U.V., Wadgaonkar P.P. Demethylation of methyl aryl ethers using pyridine hydrochloride in solvent-free conditions under microwave irradiation. // J. Chem. Res. (S). -1999.-P. 394−395
297. Bhat R.G., Ghosh Y., Chandrasekaran S. A mild and selective method for TV-dealkylation of tertiary amines. // Tetrahedron Lett. 2004. — V. 45. — P. 7983−7985
298. Fletcher S., Gunning P.T. Mild, efficient and rapid O-debenzylation of ortho-substituted phenols with trifluoroacetic acid. // Tetrahedron Lett. -2008.-V. 49.-P. 4817−4819
299. Abel A.M., Carnell A.J., Davis J.A., Paylor M. Synthesis of potential buprenorphine intermediates by selective microbial N- and O-demethylation. // Biotechnol. Lett. 2002. — V. 24. — P. 1291−1294
300. Mitscher L.A., Andres W.W., Morton G.O., Patterson E.L. Microbiological transformation of 6,14-ewdo-ethanotetrahydrothebaine alkaloids. // Experientia. 1968. — V. 24. — P. 133−134
301. Groger D., Schmauder H.P. Micribial transformation of thebaine. // Experientia. 1969. — V. 25. — P. 95−96
302. Madyastha K.M., Reddy G.V.B. Mucor piriformis, an efficient N-dealkylating reagent for thebaine and its TV-variants. // J. Chem. Soc. Perkin Trans. 1.-1994.-P. 911−912
303. Small L., Fitch H.M., Smith W.E. The addition of organomagnesium halides to pseudocodeine types. II. Preparation of nuclear alkylated morphine derivatives. // J. Amer. Chem. Soc. 1936. — V. 58. — P. 14 574 1463
304. Small L.F., Turnbull S.G., Fitch H.M. The addition of organomagnesium halides to pseudocodeine types. IV. Nuclear-substituted morphine derivatives. // J. Org. Chem. 1938. — V. 3. — P. 204−232
305. Sargent L.J., May E.L. Agonists-antagonists derived from desomorphine and metopon. // J. Med. Chem. 1970. — V. 13. — P. 1061 -1063
306. Gates M., Boden R.M., Sundararaman P. Derivatives of the thebaine anion. 2. 5-Methylmorphine, 5-methylcodeine, 5-methylheroin and some related compounds. // J. Org. Chem. 1989. — V. 54. — P. 972−974
307. Schmidhammer H., Mayer-Valkanover K., Walla-Kugler M. 183. 5-Methylnaloxone and 5-methylnaltrexone: Synthesis and pharmacological evaluation. // Helv. Chim. Acta. 1990. — V. 73. — P. 1986−1990
308. Krassnig R., Schmidhammer H., Wurst K. A novel method for the introduction of a 5/?-methyl group into 4,5a-epoxymorphinan-6-ones via the enol ether. // Helv. Chim. Acta. 2000. — V. 83. — P. 380−383
309. Proksa В., Voticky Z., Molnar L., Putek J., Stefek M. lO-Oxomorphine, a decomposition product of morphine // Chem. Zvesti. 1978. — V. 32. — P. 710−714
310. Boonstra В., Rathbone D.A., Bruce N.C. Engineering novel biocatalytic routes for production of semisynthetic opiate drugs. // Biomolecular Engineering. 2001. — V. 18. — P. 41−47
311. Толстикова Т.Г., Болкунов A.B., Морозова E.A., Толстиков С. Е. Тебаин как предшественник опиоидных анальгетиков. // Химия в интересах устойчивого развития. 2009. — С. 115−133
312. Коновалова Р.А., Юнусов С., Орехов А. П. Об алкалоидах дикорастущих видов мака. I. Алкалоиды Papaver Orientale и Papaver Armeniacum II Ж. общей химии. 1937. — Т. 7. — С. 1791−1796
313. Киселев В. В., Коновалова Р. А. Об алкалоидах дикорастущих видов мака. VIII. Алкалоиды Papaver Bracteatum II Ж. общей химии. 1948. -Т. 18.-С. 142−150
314. Pat. WO 2 008 048 957 AI. Process for preparing oxymorphone, naltrexone, and buprenorphine. / Huang B.-S. Publ. 24.04.2008
315. Baca C.T., Grant K.J. Take-home naloxone to reduce heroin death. // Addiction.-2005.-V. 100.-P. 1823−1831
316. Kreek M.J., LaForge K.S., Butelman E. Pharmacotherapy of addictions. // Nat. Rev. Drug Discovery. 2002. — V. 1. — P. 710−726
317. Freund M., Speyer E. Uber die Umwandlung von Thebain in Oxycodeinon und dessen Derivate. // J. Prakt. Chem. 1916. — V. 94. — P. 135−178
318. Hauser F.M., Chen Т.К., Carroll F.I. 14-Hydroxycodeinone. Improved synthesis. // J. Med. Chem. 1974. — V. 17. — P. 1117
319. Iijima I., Minamikawa J., Jacobson A.E., Brossi A., Rice K.C. Studies in the (+)-morphinan series. 5. Synthesis and biological properties of (+)-naloxone. // J. Med. Chem. 1978. — V. 21. — P. 398−400
320. Iijima I., Rice K.C., Brossi A. The oxidation of thebaine with m-chloroperbenzoic acid. Studies in the (+)-morphinan series. III. // Helv Chim. Acta. 1977. — V. 60. — P. 2135−2137
321. Weiss U. Derivatives of morphine. II. Demethylation of 14-hydroxycodeinone. 14-Hydroxymorphinone and 8,14-dihydroxydihydromorphinone. // J. Org. Chem. 1957. — V. 22. — P. 15 051 508
322. Weiss U. Derivatives of morphine. I. 14-Hydroxydihydromorphinone. // J. Amer. Chem. Soc. 1955. — V. 77. — P. 5891−5892
323. Osei-Gyimah P., Archer S. Synthesis and analgesic activity of some 14/?-substituted analogues of morphine. // J. Med. Chem. 1980. — V. 23. -P. 162−166
324. Archer S., Osei-Gyimah P. Reaction of thebaine with dinitrogen tetroxide. // J. Heterocycl. Chem. 1979. — V. 16. — P. 389
325. Allen R.M., Kirby G.W. Iodination of thebaine: a new route to 9-substituted indolinocodeinone derivatives. // J. Chem. Soc., Chem. Commun.- 1970.-P. 1346
326. Allen R.M., Kirby G.W., McDougall D.J. The nitration of thebaine with tetranitromethane. // J. Chem. Soc., Perkin Trans. 1. 1981. — P. 1143−1147
327. Pat. 3 254 088 US. Morphine derivative. / Lewenstein M.J., Gardens K., FishmanJ. -Publ. 31.05.1966
328. Gurll N.J., Reynolds D.G., Vargish T., Lechner R. Naloxone without transfusion prolongs survival and enhances cardiovascular function in hypovolemic shock. // J. Pharmacol. Exp. Ther. 1982. — V. 220. — P. 621 624
329. Holaday J.W., Faden A.I. Naloxone reversal of endotoxin hypotension suggests role of endorphins in shock. // Nature (London). 1978. — V. 275. -P. 450−451
330. DeBoeck C., van Reempts P., Rigatto H., Chernick V. Naloxone reduces decrease in ventilation induced by hypoxia in newborn infants. // J. Appl. Physiol. 1984.-V. 56.-P. 1507−1511
331. Kreek M.J., Hahn E.F., Schaefer R.A., Fishman J. Naloxone, a specific opioid antagonist, reverses chronic idiopathic constipation. // Lancet. -1983.-V. 321.-P. 261−262
332. Trenchard E., Silverstone T. Naloxone reduces the food intake of normal human volunteers. // Appetite: J. Intake Res. 1983. — V. 4. — P. 43−50
333. Cohen M.R., Cohen R.M., Pickar D., Murphy D.L. Naloxone reduces food intake in humans. 11 Psychosom. Med. 1985. — V. 47. — P. 132−138
334. Blumberg H., Dayton H.B. // In: Narcotic Antagonists. Braude M. C., Harris L. S., May E. L., Smith J. P., Hareal J. E. V. (Eds.). — Raven. — New York. — 1974.-P. 43
335. Gold M.S., Dackis C.A., Pottash A.L.C., Sternbach H.H., Annitto W.J., Martin D., Dackis M.P. Naltrexone, opiate addiction, and endorphins. // Med. Res. Rev. 1982. — V. 2. — P. 211−246
336. Boden R.M., Gates M., Ho S.P., Sundararaman P. Derivatives of the thebaine anion. 1. Structure of metopon. A direct demonstration. // J. Org. Chem. 1982. -V. 47. — P. 1347−1349
337. Currie A.C., Newbold G.T., Spring F.S. 14-Hydroxynorcodeine and its derivatives. // J. Chem. Soc. 1961. — P. 4693−4700
338. Pat. 3 332 950 US. 14-Hydroxydihydronormorphinone derivatives. / Blumberg H., Pachter I.J., Matossian Z. Publ. 25.07.1967 — Chem. Abstr. — 1967. — V. 67.-No. 100 301
339. Nagase H., Abe A., Portoghese P. S. The facility of formation of a A6 bond in dihydromorphinone and related opiates. // J. Org. Chem. 1989. — V. 54. -P. 4120−4125
340. Feinberg A.P., Creese I., Snyder S.H. The opiate receptor: A model explaining structure-activity relationships of opiate agonists and antagonists. // Proc. Natl. Acad. Sei. U.S.A. 1976. — V. 73. — P. 42 154 219
341. Schmidhammer H., Schratz A., Mitterdorfer J. Synthesis and biological evaluation of 14-alkoxymorphinans. 8. 14-methoxymetopon, an extremely potent opioid agonist. // Helv. Chim. Acta. 1990. — V. 73. — P. 1784−1787
342. Furst S., Buzas B., Friedmann T., Schmidhammer H., Borsodi A. Highly potent novel opioid receptor agonist in the 14-alkoxymetopon series. // Eur. J. Pharmacol. 1993. -V. 236. — P. 209−215
343. Zernig G., Saria A., Krassnig R., Schmidhammer H. Signal transduction efficacy of the highly potent mu opioid agonist 14-methoxymetopon. // Life Sei.-2000.-V. 66.-P. 1871−1877
344. King M.A., Su W., Nielan C.L., Chang A.H., Schutz J., Schmidhammer H., Pasternak G.W. 14-Methoxymetopon, a very potent /?-opioid analgesic with an unusual pharmacological profile. // Eur. J. Pharmacol. 2003. — V. 459. — P. 203−209
345. Freye E., Schmidhammer H., Latasch L. 14-Methoxymetopon, a potent opioid, induces no respiratory depression, less sedation, and less bradycardia than sufentanil in the dog. // Anesth. Analg. 2000. — V. 90. -P.1359−1364
346. Schutz J., Spetea M., Koch M., Aceto M.D., Harris L.S., Coop A., Schmidhammer H. Synthesis and biological evaluation of 14-alkoxymorphinans. 20. 14-Phenylpropoxymetopon: an extremely powerful analgesic. // J. Med. Chem. 2003. — V. 46. — P. 4182−4187
347. Portoghese P. S., Moe S.T., Takemori A.E. A selective opioid receptor agonist derived from oxymorphone. Evidence for separate recognition sites for Sx opioid receptor agonists and antagonists. // J. Med. Chem. 1993. -V.36.-P. 2572−2574
348. Portoghese P. S. Sultana M. Moe S.T. Takemori A.E. Synthesis of naltrexone-derived^-opioid antagonists. Role of conformation of the 8 address moiety. //J. Med. Chem. 1994. — V. 37. — P. 579−585
349. Brandt W. A uniform molecular model of? opioid agonist and antagonist pharmacophore conformations. // J. Comput.-Aided Mol. Des. 1998. — V. 12.-P. 615−621
350. Schmidhammer H., Spetea M. Synthesis of 14-alkoxymorphinan derivatives and their pharmacological actions. // In: Topics in Current Chemistry. 299. Chemistry of Opioids. -Nagase H. (Ed.). Springer. -Berlin-Heidelberg. — 2011. — P. 63−91
351. Portoghese P. S., Sultana M., Takemori A.E. Naltrindole, a highly selective and potent non-peptide ?opioid antagonist. // Eur. J. Pharmacol. 1988. -V. 146.-P. 185−186
352. Portoghese P. S., Sultana M., Takemori A.E. Design of peptidomimetic? opioid receptor antagonist using the message-address concept. // J. Med. Chem. 1990. — V. 33. — P. 1714−1720
353. Jones R.M., Hjorth S.A., Schwartz T.W., Portoghese P. S. Mutational evidence for a common tc antagonist binding pocket in the wild-type k and mutant? li K303E. opioid receptors. // J. Med. Chem. 1998. — V. 41. — P. 4911−4914
354. Portoghese P. S., Lipkowski A.W., Takemori A.E. Bimorphinans as highly selective, potent '?'-opioid receptor antagonists. // J. Med. Chem. 1987. -V. 30.-P. 238−239
355. Lewis J.W., Smith C.F.C., McCarthy P. S., Kobylecki R.J., Myers M., Haynes A.S., Lewis C.J., Waltham K. New 14-aminomorphinones and codeinones. // NIDA Res. Monogr. 1988. — V. 80. — P. 136−143
356. Aceto M.D., Bowman E.R., Harris L.S., May E.L. Dependence studies of new compounds in the rhesus monkey, rat and mouse. // NIDA Res. Monogr. 1989. — V. 95. — P. 578−631
357. Comer S.D., Burke T.F., Lewis J.W., Woods J.H. Clocinnamox: a novel, systemically active irreversible opioid antagonist. // J. Pharmacol. Exp. Ther. 1992. — V. 262.-P. 1051−1056
358. Woods J.H., Lewis J.W., Winger G., Butelman E., Broadbear J., Zernig G. Methoclocinnamox: a H partial agonist with pharmacotherapeutic potential for heroin abuse. // NIDA Res. Monogr. 1995. — V. 147. — P. 195−219
359. Kirby G., McLean D. An efficient synthesis of 14/?-aminocodeinone from thebaine. // J. Chem. Soc., Perkin Trans. 1. 1985. — P. 1443−1445
360. Janecki T., Bodalski R., Wieczorek M., Bujacz G. Horner-Wadsworth-Emmons olefination of nonstabilized phosphonates. A new synthetic approach to P,^-unsaturated amides. 11 Tetrahedron. 1995. — V. 51. — P. 1721−1740
361. Grundt P., Jales A.J., Traynor J.R., Lewis J.W., Husbands S.M. 14-Amino, 14-alkylamino- and 14-acylamino analogs of oxymorphindole. Differential effects on opioid receptor binding and functional profiles. // J. Med. Chem. -2003. V. 43.-P. 1563−1566
362. Takemori A.E., Larson D.L., Portoghese P. S. The irreversible narcotic antagonistic and reversible agonistic properties of the fumaramate methylester derivative of naltrexone. // Eur. J. Pharmacol. 1981. — V. 70. — P. 445−451
363. Portoghese P. S., Nagase H., Takemori A.E. Binaltorphimine and nor-binaltorphimine, potent and selective kappa-opioid receptor antagonists. // Life Sci. 1987. — V. 40. — P. 1287−1292
364. Portoghese P. S., Nagase H., Maloney-Hass K.E., Lin C.-E., Takemori A.E. Role of spacer and address components in peptidomimetic ?-opioid receptor antagonists related to naltrindole. // J. Med. Chem. 1991. — V. 34.-P. 1715−1720
365. Lever J.R. PET and SPECT imaging of the opioid system: receptors, radioligands and avenues for drug discovery and development. // Curr. Pharm. Des. 2007. — V. 13. — P. 33−49
366. Lever J.R., Scheffel U., Kinter C.M., Ravert H.T., Dannals R.F., Wagner H.N., Jr., Frost J.J. In vivo binding of M'-(nC.methyl) naltrindole to &¦ opioid receptors in mouse brain. // Eur. J. Pharmacol. 1992. — V. 216. — P. 459−460
367. Clayson J., Jales A., Tyacke R.J., Hudson A.L., Nutt D.J., Lewis J.W., Husbands S.M. Selective ?-opioid receptor ligands: potential PET ligands based on naltrindole. // Bioorg. Med. Chem. Lett. 2001. — V. 11. — P. 939 943
368. Akgun E., Sajjad M., Portoghese P. S. 7V1'-(/?-18 °F.fluorobenzyl)naltrindole (p-[18F]BNTI): a potential PET imaging agent for DOP receptors. // J. Label. Compd. Radiopharm. 2006. — V. 49. — P. 857−866
369. Eisenach J.C., Carpenter R., Curry R. Analgesia from a peripherally active^-opioid receptor agonist in patients with chronic pancreatitis. // Pain. -2003.-V. 101.-P. 89−95
370. Duval R.A., Allmon R.L., Lever J.R. Indium-labeled macrocyclic conjugates of naltrindole: high-affinity radioligands for in vivo studies of peripheral 5 opioid receptors. // J. Med. Chem. 2007. — V. 50. — P. 21 442 156
371. Zimmerman D.M., Leander J.D. Selective opioid receptor agonists and antagonists: Research tools and potential therapeutic agents. // J. Med. Chem. 1990. — V. 33. — P. 895−902
372. Sayre L.M., Portoghese P. S. Stereospecific synthesis of the 6oc- and 6fi-amino derivatives of naltrexone and oxymorphone. // J. Org. Chem. 1980. -V. 45.-P. 3366−3368
373. Mohamed M.S., Portoghese P. S. Stereoselectivity of the reduction of naltrexone oxime with borane. // J. Org. Chem. 1986. — V. 51. — P. 105 106
374. Cami-Kobeci G., Neal A.P., Bradbury F.A., Purington L.C., Aceto M.D., Harris L.S., Lewis J.W., Traynor J.R., Husbands S.M. Mixed к/ju oioid rceptor aonists: The 6/?-nltrexamines. // J. Med. Chem. 2009. — V. 52. — P. 1546−1552
375. Takemori A.E., Portoghese P. S. Affinity labels for opioid receptors. // Annu. Rev. Pharmacol. Toxicol. 1985. — V. 25. — P. 193−223
376. Mjanger E., Yaksh T.L. Characteristics of dose-dependent antagonism by beta-funaltrexamine of the antinociceptive effects of intrathecal -mu agonists. // J. Pharmacol. Exp. Ther. 1991. — V. 258. — P. 544−550
377. Nagase H., Hayakawa J., Kawamura K., Kawai K., Takezawa Y., Matsuura H., Tajima C., Endo T. Discovery of structurally novel opioid /c-agonist derived from 4,5-epoxymorphinan. // Chem. Pharm. Bull. 1998. — V. 46. -P. 366−369
378. Derrick I., Lewis J.W., Moynihan H.A., Broadbear J., Woods J.H. Potential irreversible ligands for opioid receptors. Cinnamoyl derivatives of ?-naltrexamine. // J. Pharm. Pharmacol. 1996. — V. 48. — P. 192−196
379. Derrick I., Moynihan H.A., Broadbear J., Woods J.H., Lewis J.W. 6N-Cinnamoyl-Analtrexamine and its p-nitro derivative. High efficacy k-opioid agonists with weak antagonist actions. I I Bioorg. Med. Chem. Lett. -1996. -V. 6.-P. 167−172
380. Le Bourdonnec B., El Kouhen R., Lunzer M.M., Law P.Y., Loh H.H., Portoghese P. S. Reporter affinity labels: An o-phthalaldehyde derivative of Analtrexamine as a fluorogenic ligand for opioid receptors. // J. Med. Chem. 2000. — V. 43. — P. 2489−2492
381. Caruso T.P., Takemori A.E., Larson D.L., Portoghese P. S. Chloroxymorphamine, and opioid receptor site-directed alkylating agent having narcotic agonist activity. // Science. 1979. — V. 204. — P. 316−318
382. Sayre L.M., Takemori A.E., Portoghese P. S. Alkylation of opioid receptor subtypes by ?¦-chlornaltrexamine produces concurrent irreversible agonistic and irreversible antagonistic activities. // J. Med. Chem. 1983. — V. 26. -P. 503−506
383. Portoghese P. S., Larsen D.L., Sayre L.M., Fries D.S., Takemori A.E. A novel opioid receptor site directed alkylating agent with irreversible narcotic antagonistic and reversible agonistic activities. // J. Med. Chem. -1980.-V. 23.-P. 233−234
384. Liu M., Sainsbury M., Carter N. The synthesis of some 6,7-annulated codeines. // J. Chem. Soc., Perkin Trans. 1. 1999. — P. 241−244
385. Portoghese P. S., Sultana M., Nagase H., Takemori A.E. Application of the message-address concept in the design of highly potent and selective non-peptide? opioid receptor antagonists. // J. Med. Chem. 1988. — V. 31. -P. 281−282
386. Mitsunobu O. The use of diethyl azodicarboxylate and triphenylphosphine in synthesis and transformation of natural products. // Synthesis. 1981. -P. 1−28
387. Stille J.K. The palladium-catalyzed cross-coupling reactions of organotin reagents with organic electrophiles New synthetic methods (58). // Angew. Chem., Int. Ed. Engl. 1986. — V. 25. — P. 508−524
388. Watanabe A., Kai Т., Nagase H. Novel synthesis of the ortho ester derivative of 4,5-epoxymorphinan. // Org. Lett. 2006. — V. 8. — P. 523 526
389. Nagase H., Fujii H. Synthesis of novel basic skeletons derived from naltrexone. // In: Topics in Current Chemistry. 299. Chemistry of Opioids. — Nagase H. (Ed.). Springer. — Berlin-Heidelberg. — 2011. — 312 pp. — P. 187−237
390. Sandermann W. Dien-Anlagerungsverbindungen des Thebains // Ber. -1938.-V. 71.-P. 648−650
391. Schopf C., von Gottberg K., Petri W. Uber Thebain-maleinsaureanhydrid, Thebainchinon, Thebainhydrochinon und dessen Saureumlagerungsprodukt, das Flavothebaon // Ann. 1938. — V. 536. — P. 216−257
392. Каневская С.И., Митрягнна С. Ф. Исследования в области тебаина. II. Изучение продукта конденсации тебаина с акролеином // Ж. общей хим. 1947. — Т. 17. — С. 1203−1207
393. Bentley K.W., Thomas A.F. The morphine-thebaine group of alkaloids. Part VI. The condensation of thebaine with dienophils. // J. Chem. Soc. -1956.-P. 1863−1867
394. Bentley K.W., Dominguez J. Flavothebaone. Part I. Preliminary work: spectral studies and acetolysis // J. Org. Chem. 1956. — V. 21. — P. 13 481 352
395. Bentley K.W., Dominguez J., Ringe J.P. Flavothebaone. Part II. Exhaustive Methylation of Flavothebaone Trimethyl Ether // J. Org. Chem. 1957. -V. 22.-P. 409−417
396. Bentley K.W., Hardy D.G. Novel analgesics and molecular rearrangements in the morphine-thebaine group. I. Ketones derived from 6,14-endoethenotetrahydrothebaine. // J. Amer. Chem. Soc. 1967. — V. 89. — P. 3267−3273
397. Bentley K.W., Hardy D.G., Meek B. Novel analgesics and molecular rearrangements in the morphine-thebaine group. II. Alcohols derived from 6,14-era/o-etheno- and 6,14-e"i/o-ethanotetrahydrothebaine. // J. Amer. Chem. Soc. 1967. — V. 89. — P. 3273−3280
398. Lewis J.W., Readhead M.J., Selby I.A., Smith A.C.B., Young C.A. Novel analgesics and molecular rearrangements in the morphine-thebaine group. Part XIX. Further Diels-Alder adducts of thebaine. // J. Chem. Soc. C. -1971.-P. 1158−1161
399. Rubenshtein R., Haviv F., Ginsburg D. Reactions of thebaine with cis- and iram-disubstituted dienophiles. // Tetrahedron. 1974. — V. 30. — P. 12 011 210
400. Horsewood P., Kirby G.W. Nitrosyl cyanide: a possible intermediate in the formation of A^-cyano-1,2-oxazines from conjugated dienes // J. Chem. Soc. D, Chem. Commun. 1971. — P. 1139−1140
401. Kirby G.W., Sweeny J.M. Nitrosocarbonyl compounds as intermediates in the oxidative cleavage of hydroxamic acids. // J. Chem. Soc., Chem. Commun. 1973. — P. 704−705
402. Gilchrist T.L., Peek M.E., Rees C.W. TV-aryl-C-nitroso-imines. // J. Chem. Soc., Chem. Commun. 1975. — P. 913−914
403. Gilchrist T.L., Harris C.J., King F.D., Peek M.E., Rees C.W. 1,2,4-Benzoxadiazines // J. Chem. Soc., Perkin Trans. 1. 1976. — P. 2161−2165
404. Kirby G.W., Sweeny J.G. Formation and dienophilic reactions of transient C-nitrosocarbonyl compounds // J. Chem. Soc., Perkin Trans. 1. 1981. -P. 3250−3254
405. Bentley K.W., Horsewood P., Kirby G.W., Singh S. Diels-Alder adducts from thebaine and nitroso-arenes. // J. Chem. Soc. D. 1969. — P. 1411a
406. Bentley K.W., Kirby G.W., Price A.P., Singh S. Nitrosation of thebaine leading to 7-substituted neopinone derivatives // J. Chem. Soc., Perkin Trans. 1. 1972. — P. 302−305
407. Kirby G.W., Bentley K.W., Horsewood P., Singh S. Cyclo-adducts of thebaine with nitrosoarenes // J. Chem. Soc., Perkin Trans. 1. 1979. — P. 3064−3066
408. Knipmeyer L.L., Rapoport H. Analgesics of the 6,14-ethenomorphinan type. 6-Deoxy-7<2-orvinols and 6-deoxy-8<2-orvinols. // J. Med. Chem. -1985.-V. 28.-P. 461−466
409. Bentley K.W., Ball J.C. Base-catalyzed rearrangements in the nepenthone series. // J. Org. Chem. 1958. — V. 23. — P. 1725−1730
410. Lewis J.W., Readhead M.J., Smith A.C.B. Novel analgesics and molecular rearrangements in the morphine-thebaine group. Part XXVI. Some reactions of the thebaine-2-chloroacrylonitrile adduct // J. Chem. Soc., Perkin Trans. 1. 1972. — P. 878−881
411. Rapoport H., Sheldrick P. The Diels-Alder reaction with thebaine. Thermal rearrangement of some adducts from acetylenic dienophiles. // J. Amer. Chem. Soc. 1963. — V. 85. — P. 1636−1642
412. Jeong I.H., Kim Y.S., Cho K.Y. Reaction of thebaine with trifluoromethyl substituted acetylenic dienophiles. // Bull. Korean Chem. Soc. 1990. — V. 11.-P. 258−260
413. Hayakawa K., Motohiro S., Fujii I., Kanematsu K. Novel addition reaction of thebaine with acetylenic dienophiles: Construction of a new morphine skeleton. // J. Amer. Chem. Soc. 1981. — V. 103. — P. 4605−4606
414. Singh A., Archer S., Hoogsteen K., Hirshfield J. Thebaine and acetylenic dienophiles. // J. Org. Chem. 1982. — V. 47. — P. 752−754
415. Hayakawa K., Fujii I., Kanematsu K. Addition reaction of thebaine and related compounds with acetylenic dienophiles: The structure-reactivity relationship. // J. Org. Chem. 1983. — V. 48. — P. 166−173
416. Singh A., Archer S., Hoogsteen K., Hirshfield J. Thebaine and acetylenic dienophiles. // J. Org. Chem. 1983. — V. 48. — P. 173−177
417. Rubenstein R., Giger R., Ginsburg D. The structure of the irradiation product of the dihydro-diels-alder adduct of thebaine with dimethyl acetylenedicarboxylate. // Tetrahedron. 1973. — V. 29. — P. 2383−2386
418. Шулыд Э.Э., Толстикова Т. Г., Толстиков С. Е., Дайбова В. Т., Шакиров М. М., Болкунов A.B., Долгих М. П. Синтез и анальгетическая активность производных пирролидиноморфинана. // Хим.-фарм. журн. -2007.-Т. 41.-С. 15−18
419. Бауман В.Т., Шульц Э. Э., Шакиров М. М., Толстиков Г. А. Синтетические трансформации изохинолиновых алкалоидов. Синтез 1-галоидзамещенных производных эндоэтенотетрагидротебаина и их поведение в реакции Хека. // Ж. органич. хим. 2007. — Т. 43. — С. 529 539
420. Бауман В.Т., Шульц Э. Э., Шакиров М. М., Толстиков Г. А. Синтетические трансформации изохинолиновых алкалоидов. Синтез новых производных дигидротебаингидрохинона. // Изв. академии наук, серия хим. 2007. — С. 1206−1214
421. Толстикова Т.Г., Морозова Е. А., Болкунов A.B., Долгих М. П., Бауман В. Т., Толстиков С. Е., Шульц Э. Э. Влияние атома брома на анальгетическую активность производных пирролидиноморфинана. // Вопросы биол. мед. и фарм. химии. 2007. — С. 33−35
422. Bentley K.W., Hardy D.G. New potent analgesics in the morphine series. // Proc. Chem. Soc. 1963. — P. 220
423. Laus G., Schutz J., Schottenberger H., Andre M., Wurst К., Spetea M., Ongania K.-H., Muller A.G., Schmidhammer H. Etorphine-related ferrocenyl-substituted morphinan alkaloids. // Helv. Chim. Acta. 2003. -V. 86.-P. 3274−3280
424. Hatzoglou A., Bakogeorgou E., Castanas E. The antiproliferative effect of opioid receptor agonists on the T47D human breast cancer cell line, is partially mediated through opioid receptors. // Eur. J. Pharmacol. 1996. -V. 296.-P. 199−207
425. Coop A., Norton C.L., Berzetei-Gurske I., Burnside J., Toll L., Husbands S.M., Lewis J.W. Structural determinants of opioid activity in the orvinols and related structures: Ethers of orvinol and isoorvinol. // J. Med. Chem. -2000.-V. 43.-P. 1852−1857
426. Czaky В., Marton J., Berenyi S., Gach K., Fichna J., Storr M., Tyth G., Sipos A., Janecka A. Synthesis and opioid activity of novel 6-substituted-6-demethoxyethenomorphinans. // Bioorg. Med. Chem. 2010. — V. 18. — P. 3535−3542
427. Seki I. Studies on the morphine alkaloids and its related cCompounds. XVII. One-step preparations of enol ether and pyrrolidinyl dienamine of normorphinone derivatives. // Chem. Pharm. Bull. 1970. — V. 18. — P. 671−676
428. Marton J., Hosztafi S., Berenyi S., Simon C., Makleit S. Herstellung von 6,14-Ethenomorphinan-Derivaten. // Monatsh. Chem. 1994. — V. 125. -P. 1229−1239
429. Chen W., Parrish D.A., Deschamps J.R., Coop A. Functionalization of the 6,14-bridge of the orvinols. 1. Preparation and Diels-Alder reaction of 7-phenylsilylthebaines. // Helv. Chim. Acta. 2005. — V. 88. — P. 822−829
430. Soeiro O.M., Da Silva A.J.R., Barnes R.A. Transformation products of salutarine and their 13C-nuclear magnetic resonance spectra. // Chem. Pharm. Bull. 1982. — V. 30. — P. 1998−2002
431. Chen W., Metcalf M.D., Coop A., Flippen-Anderson J.L., Deschamps J.R. 5-Butylthevinone: stereochemistry of the Diels-Alder reaction of 5-butylthebaine with 3-buten-2-one. // Acta Crystallogr., Sect. E. 2003. — V. 59. — P. ol 14-oll6
432. Pratt L.P., Streitwieser A. Ab initio analysis of pentadienyllithium, pentadienylsodium, and the pentadienyl ions. // J. Org. Chem. 2000. — V. 65.-P. 290−294
433. Zhdankin V.V., Stang P.J. Recent developments in the chemistry of polyvalent iodine compounds. // Chem. Rev. 2002. — V. 102. — P. 25 232 584
434. Lutz R.E., Small L.F. Reductions in the morphine series. I. Dihydropseudocodeine. // J. Amer. Chem. Soc. 1932. — V. 54. — P. 47 154 730
435. Small L., Lutz R.E. Reduction studies in the morphine series. III. Dihydro-y-isomorphine. // J. Amer. Chem. Soc. 1934. — V. 56. — P. 1928−1930
436. Pat. 3 433 791 US. Endoethano nor oripavines and nor thebaines. / Bentley K. W. Publ. 18.03.1969. — Chem. Abstr. — 1969. — V. 70. — No. 78218s
437. Lewis J.W., Readhead M.J. Reduction of 14-alkenylcodeinones by sodium borohydride in pyridine. // Tetrahedron. 1968. — V. 24. — P. 1829−1833
438. Fulmor W., Lancaster J.E., Morton G.O., Brown J.L., Howell C.F., Nora C.T., Hardy R.A., Jr. Nuclear magnetic resonance studies in the 6,14-endo-ethenotetrahydrothebaine series. // J. Amer. Chem. Soc. 1967. — V. 89. -P. 3322−3330
439. Lee K.O., Akil H., Woods J.H., Traynor J.R. Differential binding properties of oripavines at cloned p.- and 8-opioid receptors. // Eur. J. Pharmacol. -1999.-V. 378.-P. 323−330
440. Lewis J.W. Buprenorphine. // Drug Alcohol Depend. 1985. — V. 14. — P. 363−372
441. Husbands S.M., Lewis J.W. Structural determinants of efficacy for k opioid receptors in the orvinol series: 7,7-Spiro analogues of buprenorphine. // J. Med. Chem. 2000. — V. 43. — P. 139−141
442. Abdelhamid E.E., Sultana M., Portoghese P. S., Takemori A.E. Selective blockage of delta opioid receptors prevents the development of morphine tolerance and dependence in mice. // J. Pharmacol. Exp. Ther. 1991. — V. 258.-P. 299−303
443. Flippen-Anderson J.L., George C. X-Ray crystal structures of potent opioid receptor ligands: etonitazene, cis-(+)-3-methylfentanyl, etorphine, diprenorphine, and buprenorphine. // Heterocycles. 1994. — V. 39. — P. 751−766
444. Kratochvil B., Husak M., Bulej P., Jegorov A. The molecular and crystal structure of buprenorphine hydrochloride, a morphine analog. // Coll. Czech. Chem. Commun. 1994. — V. 59. — P. 2472−2480
445. Cowan A., Lewis J.W. Buprenorphine: combatting drug abuse with a unique opioid. Wiley-Liss. — 1995
446. Jasinski D.R., Pevnick J.S., Griffith J.D. Human pharmacology and abuse potential of the analgesic buprenorphine. A potential agent for treating narcotic addiction. // Arch. Gen. Psych. 1978. — V. 35. — P. 501−516
447. Vocci F., Ling W. Medications development: success and challenges. // Pharmacol. Ther. 2005. — V. 108. — P. 94−108
448. Compton P., Ling W., Moody D., Chiang N. Pharmacokinetics, bioavailability and opioid effects of liquid versus tablet buprenorphine. // Drug Alcohol Depend. 2006. — V. 82. — P. 25−31
449. Tzschentke T.M. Behavioral pharmacology of buprenorphine, with a focus on preclinical models of reward and addiction. // Psychopharmacology. -2002.-V. 161.-P. 1−16
450. Cowan A. Buprenorphine: the basic pharmacology revisited. // J. Addict. Med. 2007. — V. 1. — P. 68−72
451. Lewis J.W., Husbands S.M. The orvinols and related opioids High affinity ligands with diverse efficacy profiles. // Curr. Pharm. Des. — 2004. — V. 10. -P. 717−732
452. Pat. 2 005 007 0564A1 US. Oripavine derivatives and their uses as medicines. / Zhong B., Gong Z., Wang Y., Liu Y. Publ. 31.03.2005
453. Pat. 3 931 189 US. N-(Heteroary 1-methyl)-6,14-(endoethano or endoetheno)-7a-hydroxyalkyl-tetrahydro-nororipavines or-northebaines and salts thereof. / Langbein A., Merz H., Walther G., Stockhaus K. Publ. 06.01.1976
454. Pat. 116 8377A CN. Novel buprenophine analgesic analogues. / Kim Y.-H., Park J.-K., Kim K. Publ. 24.12.1997
455. Pat. 200 912 2436A2 WO. An improved process for the preparation of morphinane analogues. / Patel N.S., Kilaru S., Thennati R. Publ. 10.08.2009
456. Marton J., Szabo Z., Hosztafi S. Herstellung von 6,14-Ethenomorphinan-Derivaten. // Lieb. Ann. Chem. 1993. — P. 915−919
457. Pat. 166 095 B1 PL. Sposob wytwarzania vV-cyklopropylometylo-7? -(S)-1 -hydroksy-1,2,2-trimetylopropylo.-e"ofo-etano-6,7,8,14-tetrahydronororipaviny. / Stelmach P., Bobrowska E., Falek K. Publ. 03.31.1995
458. Abel A.M., Allan G.R., Carnell A.J., Davis J.A. A novel regiospecific Nto O-methyl transferase activity in the biotransformation of a thebainederivative with Cunninghamella echinulata NRRL 1384. // J. Chem. Soc., Chem. Commun. 2002. — P. 1762−1763
459. Pat. 200 603 5195A1 WO. Preparation of opiate analgesics by reductive alkylation. / Goodwin N.J., Mitchell M., Thomson N.K., Wilson G.S., Young M.J. Publ. 06.04.2006
460. Debrabandere L., Van Boven M., Daenens P. Synthesis of iodobuprenorphine for use in radioimmunoassay. // J. Label. Сотр. Radiopharm. 1992. -V. 31. — P. 575−588
461. Pat. 200 417 5706A JP. New buprenorphine ester derivative, method for preparing the same and analgesic composition having persistency of validity for many hours. /OS.- Publ. 24.06.2004
462. Pat. 142 2230A1 EP. Novel ester derivatives of buprenorphine and their preparation processes, and long acting analgestic pharmaceutical compositions. / Wang J.-J. Publ. 26.05.2004
463. Park H.S., Lee H.Y., Kim Y.H., Park J.K., Zvartau E.E., Lee H. A highly selective^-opioid receptor agonist with low addictive potential and dependence liability. // Bioorg. Med. Chem. Lett. 2006. — V. 16. — P. 3609−3613
464. Pat. 144 243 EP. Analgesic compositions / Lewis J.W., Lloyd-Jones J.G. -Publ. 12.06.1985
465. Пат. 225 5737C2 РФ. Анальгезирующие композиции, содержащие бупренорфин. / Чаплео К. Б., Маккормак К., Вэйри Н. К. Б.И. — 2005. — № 19
466. Pat. 194 3575A CN. Abuse potential low compound buprenorphine hydrochloride naloxone hydrochloride sublingual tablet. / Xu J.Y. Publ. 11.04.2007
467. Pat. 200 810 4737A1 WO. Improved medicinal compositions comprising buprenorphine and naloxone. / Chapleo C.B., Hyde N. Publ. 04.09.2008
468. Pat. 200 810 4738A1 WO. Improvements in and relating to medicinal compositions. / Chapleo C.B., Hyde N. Publ. 04.09.2008
469. Pat. 244 7015A GB. Analgesic composition comprising a specific ratio of buprenorphine and naltrexone. / Chapleo C.B., Hyde N. Publ. 03.09.2008
470. Pat. 244 7016A GB. Buprenorphine/naloxone compositions. / Chapleo C.B., Hyde N. Publ. 03.09.2008
471. Pat. 216 7663A GB. Analgesics containing buprenorphine and naltrexone. / Lewis J.W., Lloyd-Jones J.G. Publ. 04.06.1986
472. Pat. 200 810 473 5A1 WO. Improved medicinal compositions comprising buprenorphine and naltrexone. / Chapleo C.B., Hyde N. Publ. 04.09.2008
473. Pat. 244 7014A GB. Analgesic composition comprising a specific ratio of buprenorphine and naltrexone. / Chapleo C.B., Hyde N. Publ. 03.09.2008
474. Pat. 200 810 473 6A1 WO. Improved medicinal compositions comprising buprenorphine and nalmefene. / Chapleo C.B., Hyde N. Publ. 04.09.2008
475. Pat. 244 7013A GB. Analgesic composition containing buprenorphone and nalmefene. / Chapleo C.B., Hyde N. Publ. 03.09.2008
476. Semmelhack M.F. Transition metal arene complexes: nucleophilic addition. // In: Comprehensive Organometallic Chemistry II. Abel E.W., Stone F.G.A., Wilkinson G. (Eds.). — Pergamon Press. — Oxford. — UK. — 1995. -V. 12.-P. 979−1016
477. M.F. Semmelhack. Transition metal arene complexes: ring lithiation. // In: Comprehensive Organometallic Chemistry II. Abel E.W., Stone F.G.A., Wilkinson G. (Eds.). — Pergamon Press. — Oxford. — UK. — 1995. — V. 12. -P. 1017−1038
478. Rosillo M., Dominguez G., Perez-Castells J. Chromium arene complexes in organic synthesis. // Chem. Soc. Rev. 2007. -V. 36. — P. 1589−1604
479. Pape A.R., Kaliappan K.P., Ktindig E.P. Transition-metal-mediated dearomatization reactions. // Chem. Rev. 2000. — V. 100. — P. 2917−2940
480. Berger A., Djukic J.-P., Michon C. Metalated {rf-arene)tricarbonylchromium complexes in organometallic chemistry. // Coord. Chem. Rev. 2002. — V. 225. — P. 215−238
481. Калинин B.H. Аренхромтрикарбонилы в органическом синтезе.
482. Yen. хим. 1987. — Т. 56. — С. 1190−1227
483. Salzer A. Chiral mono- and bidentate ligands derived from chromium arene complexes synthesis, structure and catalytic applications. // Coord. Chem. Rev. — 2003. — V. 242. — P. 59−72
484. Bolm C., Muniz K. Planar chiral arene chromium (O) complexes: potential ligands for asymmetric catalysis. // Chem. Soc. Rev. 1999. — V. 28. — P. 51−59
485. Rose-Munch F., Rose E. Application of ('? 6-arene) chromium tricarbonyl complexes in organic synthesis: Nucleophilic aromatic substitution and lithiation. // Current Org. Chem. 1999. — V. 3. — P. 445−467
486. Semmelhack M.F. Arene-metal complexes in organic synthesis. // Ann. N. Y. Acad. Sci. 1977. — V. 295. — P. 36−51
487. Bunnett J.F., Hermann H. Kinetics of reactions of amines with tricarbonyl (fluorobenzene)chromium. // J. Org. Chem. 1971. — V. 36. — P. 4081−4088
488. Pfletschinger A., Thargel T.K., Bats J.W., Schmalz H.-G., Koch W. Structural and energetical characterization of reactive intermediates derived from toluene-Cr (CO)3. // Chem. Eur. J. 1999. — V. 5. — P. 537−545
489. Jaouen G., Top S., McGlinchey M.J. A carbon-13 NMR spectroscopic study of a Cr (CO)3-stabilised benzyl anion. // J. Organomet. Chem. 1980. -V. 195.-P. C9-C12
490. Merlic C.A., Hietbrink B.N., Houk K.N. Donor and acceptor properties of the chromium tricarbonyl substituent in benzylic and homobenzylic anions, cations, and radicals. // J. Org. Chem. 2001. — V. 66. — P. 6738−6744
491. Merlic C.A., Walsh J.C. The tricarbonylchromium template for stereocontrol in radical reactions of arenes. // J. Org. Chem. 2001. — V. 66. — P. 2265−2274
492. Top S., Jaouen G. Synthese directe de composes areniques bis-chrome tricarbonyles. // J. Organometal. Chem. 1979. — V.182. — P. 381−392
493. Rosea S.I., Rosea S. // Revista de Chemie (Bucharest). 1964. — V. 25. -P. 461 (Uht. no: 523.)
494. Semmelhack M.F., Hall H.T. Intermediates in the reaction of carbanions with -^(chlorobenzene)chromium tricarbonyl. // J. Amer. Chem. Soc. -1974. V. 96. — P. 7092−7094
495. Semmelhack M.F., Hall H.T. Phenylation of carbanions by 7t-(chlorobenzene)chromium tricarbonyl. // J. Amer. Chem. Soc. 1974. — V. 96.-P. 7091−7092
496. Card R.J., Trahanovsky W.S. Arene-metal complexes. 12. Reaction of (7f-benzene)tricarbonylchromium with «-butyllithium. // J. Org. Chem. 1980. -V. 45.-P. 2555−2559
497. Card R.J., Trahanovsky W.S. Arene-metal complexes. 13. Reaction of substituted (benzene)tricarbonylchromium complexes with «-butyllithium. // J. Org. Chem. 1980. — V. 45. — P. 2560−2566
498. Hudecek M., Toma S. An improved method for the synthesis of r|6-arenetricarbonylchromium complexes. // J. Organomet. Chem. 1990. — V. 393.-P. 115−118
499. Ratni H., Kundig E.P. Synthesis of (-)-lasubine (I) via a planar chiral (T6-arene)Cr (CO)3. complex. // Org. Lett. 1999. — V. 1. — P. 1997−1999
500. Kundig E.P., Chaudhuri P.D., House D., Bernardinelli G. Catalytic enantioselective hydrogenolysis of Cr (CO)3(5,8-dibromonaphthalene). // Angew. Chem., Int. Ed. 2006. — V. 45. — P. 1092−1095
501. Baudoin O. The asymmetric Suzuki coupling route to axially chiral biaryls. // Eur. J. Org. Chem. 2005. — P. 4223−4229
502. Bringmann G., Mortimer A.J.P., Keller P.A., Gresser M.J., Garner J., Breuning M. Atroposelective synthesis of axially chiral biaryl compounds. // Angew. Chem., Int. Ed. 2005. — V. 44. — P. 5384−5427
503. Lee Y.T., Choi S.Y., Lee S.I., Chung Y.K., Kang T.J. Microwave-assisted synthesis of (^16-arene)tricarbonylchromium complexes. // Tetrahedron. Lett. 2006. — V. 47. — P. 6569−6572
504. Kundig E.P., Perret C., Spichiger S., Bernardinelli G. Naphthalene complexes: V. Arene exchange reactions in naphthalenechromium complexes. // J. Organomet. Chem. 1985. — V. 286. — P. 183−200
505. McCarthy J.R., Wiedeman P.E., Schuster A.J., Whitten J.P., Barbuch R.J., Huffman J.C. Stereospecific syntheses of the four diastereomeric 2-amino-5-phenoxycyclopentanols. // J. Org. Chem. 1985. — V. 50. — P. 3095−3 103 568
506. Schollkopf K., Stezowski J.J., Effenberger F. Aminobenzenes. 18. Crystal and molecular structures of novel (arene)chromium tricarbonyl complexes. // Organometallics. 1985. — V. 4. — P. 922−929
507. Nagelberg S.B., Reinhold C.E., Willeford B.R., Bigwood M.P., Molloy K.C., Zuckerman J.J. Tricarbonylchromium complexes of (CH3)2EAr2 ligands (E = C, Si, Ge, Sn, and Pb- Ar = C6H5, CH2C6H5, and p-C6H4CH3). // Organometallics. 1982. -V. 1. — P. 851−858
508. Kaganovich V.S., Rybinskaya M.I. Heterometallic n, 7i-complexes of transition metals based on mesitylacetonitrile. // J. Organomet. Chem. -1991.-V. 407.-P. 215−224
509. Pruett R.L. Synthesis of cyclopentadienyl-metal carbonyls. // Prep. Inorg. React. 1965.-V. 2.-P. 187v s
510. Hudecek, M.- Toma, S. A simple route to (-/ -arene)tricarbonylchromium complexes and a systemic study of different catalysts for complexation of arenes with Cr (CO)6. // J. Organomet. Chem. 1991. — V. 406. — P. 14 7151v
511. Hrnciar P., Hudecek M., Magomedov G.K.I., Toma S. Exploration of the new method for the synthesis of r)6-arenetricarbonylchromium complexes. The scope and limitations. // Collect. Czech. Chem. Commun. 1991. — V. 56.-P. 1477−1481
512. Sergheraert C., Brunet J.-C., Tartar A. Incorporation of the tricarbonylchromium ligand in aqueous media on the side chain of aromatic amino-acids. // J. Chem. Soc., Chem. Commua 1982. — P. 1417−1418
513. Nicholls B., Whiting M.C. The organic chemistry of the transition elements. Part I. Tricarbonylchromium derivatives of aromatic compounds. // J. Chem. Soc. 1959. — P. 551−556
514. Strohmeier W. Eine verbesserte Darstellung von Aromaten- und Cycloheptatrien-Chromtricarbonylen. // Chem. Ber. 1961. — V. 94. — P. 2490−2493
515. Semmelhack M.F., Thebtaranonth Y., Keller L. Formation of fused, spiro, and metacyclophane rings via intramolecular carbanion attack on arene-chromium complexes. // J. Amer. Chem. Soc. 1977. — V. 99. — P. 959−961
516. Mahaffy C.A.L., Pauson P.L. (?5-Arene)tricarbonylchromium complexes. //Inorg. Synth. 1979.-V. 19.-P. 154−158
517. Strohmeier W. Eine verbesserte Darstellung von Aromaten- und Cycloheptatrien-Chromtricarbonylen. // Chem. Ber. 1961. — V. 94. — P. 2490−2493
518. Semmelhack M.F., Thebtaranonth Y., Keller L. Formation of fused, spiro, and metacyclophane rings via intramolecular carbanion attack on arene-chromium complexes. // J. Amer. Chem. Soc. 1977. — V. 99. — P. 959−961
519. Mahaffy C.A.L. The Synthesis and characterization of the tricarbonylchromium complexes of dimethylaniline, dimethylanisole and related complexes. // Synth. React. Inorg. Met.-Org. Chem. 1984. — V. 14.-P. 679−687
520. Khand I.U., Mahaffy C.A.L., Pauson P.L. // J. Chem. Research (M). -1978. P. 4454 (IJht. no: 523.)
521. Mahaffy C.A.L. The synthesis and characterization of tricarbonylchromium complexes of substituted anilines and fluorobenzenes. // J. Organometal. Chem. 1984. — V. 262. — P. 33−37
522. Knox G.R., Leppard D.G., Pauson P.L., Watts W.E. Tricarbonyl (phenylacetylene)chromium and tricarbonyl (styrene)chromium. // J. Organomet. Chem. 1972. — V. 34. — P. 347
523. Edelmann F.T. Synthesis and characterization of deuterium-labelled (fulvene)M (CO)3 complexes (M = Cr, Mo). // Inorg. Chim. Acta. 2004. -V. 357.-P. 4592−4595
524. Oprunenko Yu.F., Malugina S.G., Ustynyuk Yu.A., Ustynyuk N.A., Kravtsov D.N. Inter-ring rf: rf haptotropic rearrangements in naphthalenetricarbonylchromium complexes. // J. Organomet. Chem. -1988.-V. 338.-P. 357−368
525. Rausch M.D. Recent studies in metal-cyclopentadienyl and metal-arene chemistry. // Pure Appl. Chem. 1972. — V. 30. — P. 523−538
526. Moser G.A., Rausch M.D. The utility of triamminetricarbonylchromium, (NH3)3Cr (CO)3, in the synthesis of arenetricarbonylchromium complexes. // Synth. React. Inorg. Metal-Org. Chem. 1974. — V. 4. — P. 37−48
527. Rausch M.D., Moser G.A., Zaiko E.J., Lipman A.L., Jr. Organometallic л-complexes: XX. The preparation of styrenetricarbonylchromium. // J. Organometal. Chem. 1970. — V. 23. — P. 185
528. Vebrel J., Mercier R., Belleney J. A direct and efficient complexation of some indenes and dihydronaphthalenes with (NH3)3Cr (CO)3. // J. Organometal. Chem. 1982. — V. 235. — P. 197−200
529. Amor A.B.H., Top S., Meganem F., Jaouen G. Selective functionalization of crown ethers via arene chromium tricarbonyl complexes. // J. Organometal. Chem. 2005. — V. 690. — P. 847−856
530. Kundig Е.Р., Lomberget Т., Bragg R., Poulard С., Bernardinelli G. Desymmetrization of a meso-diol complex derived from Cr (CO)3(//6−5,8-naphthoquinone).: use of new diamine acylation catalysts. // Chem. Commun. 2004. — P. 1548−1549
531. Kundig E.P., Perret С., Spichiger S., Bernardinelli G. Naphthalene complexes: V. Arene exchange reactions in naphthalenechromium complexes. // J. Organomet. Chem. 1985. — V. 286. — P. 183−200
532. Dotz K.H., Stendel J., Muller S., Nieger M., Ketrat S., Dolg M. Haptotropic metal migration in densely substituted hydroquinoid phenanthrene Cr (CO)3 complexes. // Organometallics. 2005. — V. 24. — P. 3219−3228
533. Englert U., Hu C., Salzer A., Alberico E. Conformationally constrained diphosphines derived from (^6-(5)-l-(dimethylamino)indane)Cr (CO)3: Synthesis and application in enantioselective hydrogenation. // Organometallics. 2004. — V. 23. — P. 5419−5431
534. Mitchell R.H., Brkic Z., Berg D.J., Barclay T.M. Effective aromaticity of tricarbonylchromiumbenzene, about 25% enhanced over that of benzene: Structural evidence from a complexed benzannulene. // J. Amer. Chem. Soc. 2002. — V. 124. — P. 11 983−11 988
535. Desobry V., Kundig E.P. A 13C-NMR. Study of naphthalene chromium complexes. Correlation with reactivity: Nucleophilic aromatic substitution reactions. // Helv. Chim. Acta. 1981. — V. 64. — P. 1288−1297
536. Kayran C., Ozkar S. Synthesis and NMR study of (D6-l, 4-dipheny 1−1,3-butadiene)tricarbonylchromium (O). // Z. Naturforsch., B: Chem. Sei. -1992.-V. 47.-P. 1051−1053
537. Uemura M., Kobayashi T., Isobe K., Minami T., Hayashi Y. Stereoselective synthesis of (?6-arene)Cr (CO)3 complexes possessing a chiral center at the benzylic position. // J. Org. Chem. 1986. — V. 51. — P. 2859−2863
538. Alexakis A., Mangeney P., Marek I., Rose-Munch F., Rose E., Semra A., Robert F. Resolution and asymmetric synthesis of ortho-substituted (benzaldehyde)tricarbonylchromium complexes. // J. Amer. Chem. Soc.1992.-V. 114.-P. 8288−8290
539. Kondo Y., Green J.R., Ho J. Tartrate-derived aryl aldehyde acetals in the asymmetric directed metalation of chromium tricarbonyl arene complexes. //J. Org. Chem. 1993.-V. 58.-P. 6182−6189
540. Kiindig E.P. Leresche J. Saudan L. Bernardinelli G. Chiral tricarbonyl (A/6-cyclobutabenzene)chromium complexes. Diastereoselective synthesis and use in asymmetric cycloaddition reactions. // Tetrahedron. 1996. — V. 52. -P. 7363−7378
541. Fretzen A., Ripa A., Liu R., Bernardinelli G., Kiindig E.P. 1,2-Disubstituted (^6-Arene)Cr (CO)3. complexes by sequential nucleophilic addition/e"do-hydride abstraction. // Chem. Eur. J. 1998. — V. 4. — P. 251 259
542. Razuvaev G.A., Artemov A.N., Aladjin A.A., Sirotkin N.I. Tricarbonylchromiumphenylboric acid. // J. Organomet. Chem. 1976. — V. 111.-P. 131−135
543. Strotmann M., Buttenschon H. Preparation of chiral amine carbonyl chromium (O) complexes with (norbornadiene)Cr (CO)4. as the complexation reagent. // Eur. J. Org. Chem. 2000. — P. 2273−2284
544. Kostemans G.B.M., Bobeldijk M., Kwakman P.J., de Wolf W.H., Bickelhaupt F. Photochemical synthesis of arenetricarbonylchromium (O) complexes: scope and limitations. // J. Organomet. Chem. 1989. — V. 363. -P. 291−296
545. Ardon M., Hogarth G., Oscroft D.T.W. Organometallic chemistry in a conventional microwave oven: the facile synthesis of Group 6 carbonyl complexes. // J. Organomet. Chem. 2004. — V. 689. — P. 2429−2435
546. Ghavshou M., Widdowson D.A. Synthetic applications of tricarbonyl-//6-arenechromium (O) complexes: the synthesis of benzo-fused heterocycles. // J. Chem. Soc., Perkin 1. 1983. — P. 3065−3070
547. Kundig E.P., Desobry V., Simmons D.P., Wenger E. Thermodynamic control of regioselectivity in the addition of carbanions to (arene)tricarbonylchromium complexes. // J. Amer.Chem. Soc. 1989. -V. 111.-P. 1804−1814
548. Dotz K.H. Synthesis of the naphthol skeleton from pentacarbonyl-methoxy (phenyl)carbene.chromium (0) and tolan. // Angew. Chem., Int. Ed. Engl. 1975. — V. 14. — P. 644−645
549. Minatti A., Dotz K.H. Enantioselective total synthesis of (-)-curcuquinone via regioselective chromium-mediated benzannulation. // J. Org. Chem. -2005. V. 70. — P. 3745−3748
550. Kotha S., Misra S., Haider S. Benzannulation. // Tetrahedron. 2008. — V. 64.-P. 10 775−10 790
551. Dotz K.H., Tomuschat P. Annulation reactions of chromium carbene complexes: scope, selectivity and recent developments. // Chem. Soc. Rev.- 1999.-V. 28.-P. 187−198
552. Waters M.L., Wulff W.D. The synthesis of phenols and quinones via Fischer carbene complexes. // Org. React. 2008. — V. 70. — P. 121−623
553. Dotz K.H., Stendel J., Jr. // In: Modern Arene Chemistry. Astruc D. (Ed).- Wiley-VCH. Weinheim (Bergstr.). — 2002. — P. 250−296
554. Wulff W.D. Transition metal carbene complexes: alkyne and vinyl ketene chemistry // In: Comprehensive Organometallic Chemistry. — Abel E.W., Stone F.G.A., Wilkinson G. (Eds.). Pergamon Press. — Oxford. — 1995. -V. 12.-P. 469−547
555. Schore N.E. Transition metal-mediated cycloaddition reactions of alkynes in organic synthesis. // Chem. Rev. 1988. — V. 88. — P. 1081−1119
556. Dotz K.H. Carbene complexes in organic synthesis New synthetic methods (47). // Angew. Chem. Int. Ed. 1984. — V. 23. — P. 587−608
557. Fraser R.R., Mansour T.S. Acidities of arenetricarbonylchromium (O) complexes in tetrahydrofuran. // J. Organometal. Chem. 1986. — V. 310. -P. C60-C62
558. Несмеянов A.H., Колобова H.E., Анисимов K.H., Макаров Ю. В. Металлирование бензолхромтрикарбонила. // Изв. АН СССР, серия хим.-1968.-С. 2665
559. Fischer Е.О. Structure, bonding and reactivity of (stable) transition metal carbonyl carbene complexes. // Pure Appl. Chem. 1970. — V. 24. — P. 407−423
560. Semmelhack M.F., Hall H.T., Yoshifugi M., Clark G. Reactions of carbanions with^{benzenechromium} tricarbonyl. Nucleophilic aromatic substitution for hydride. // J. Amer. Chem. Soc. 1975. — V. 97. — P. 12 471 248
561. Semmelhack M.F., Hall H.T., Yoshifugi M. rf-Cyclohexadienyltricarbonylchromium (O) intermediates in the reaction of carbanions with^{-arenetricarbonylchromium} (O). // J. Amer. Chem. Soc. -1976.-V. 98.-P. 6387−6389
562. Semmelhack M.F., Clark G. meto-Substituted aromatics by carbanion attack on^anisole and^{toluenechromium} tricarbonyl. // J. Amer. Chem. Soc.- 1977.-V. 99.-P. 1675−1676
563. Trahanovsky W.S., Card R.J. Arene-metal complexes. IV. Base-catalyzed stereoselective hydrogen-deuterium exchange of benzylic protons of tricarbonylchromium (0)-complexed alkylbenzenes. // J. Amer. Chem. Soc. 1972. — V. 94. — P. 2897−2898
564. Broaddus C.D. Homogeneous metalation of alkylbenzenes. // J. Org. Chem. 1970. — V. 35.-P. 10−15
565. Dixon J.A., Fishman D.H. Alkylation of aromatic hydrocarbons by alkyllithium reagents. // J. Amer. Chem. Soc. 1963. — V. 85. — P. 13 561 357
566. Dua S.S., Gilman H. Contrasts between i-butyllithium and «-butyllithium in some exchange reactions. // J. Organometal. Chem. 1974. — V. 64. — P. C1-C2
567. Roberts J.D., Curtin D.Y. Metalation of benzotrifluoride. // J. Amer. Chem. Soc. 1946. — V. 68. — P. 1658−1660
568. Lepley A.R., Khan W.A., Guimanini A.B., Guimanini A.G. Metallation of Д iV-Dimethylaniline. // J. Org. Chem. 1966. — V. 31. -P. 2047−2051
569. Хвостик Г. М., Поддубный И. Я., Соколов B.H., Бабкина О. Н. Изучение ионной природы н-BuLi методом электродиализа // Ж. физич. химии. -1970. Т. 44. — С. 2642−2543
570. Rose-Munch F., Rose Е. Cine and tele nucleophilic substitutions in {rf-arenetricarbonylchromium and tricarbonyl (^-cyclohexadienytymanganese complexes. // Eur. J. Inorg. Chem. 2002. — P. 1269−1283
571. Semmelhack M.F., Clark G.R., Garcia J.L., Harrison J J., Thebtaranonth Y., Wulff W., Yamashita A. Addition of carbon nucleophiles to arene-chromium complexes. // Tetrahedron. 1981. — V. 37. — P. 3957−3965
572. Kiindig E.P., Liu R., Ripa A. A new asymmetric synthesis of tricarbonylchromium complexes of ori/zo-substituted benzaldehydes. Preliminary communication. // Helv. Chim. Acta. 1992. — V. 75. — P. 2657−2660
573. Fretzen A., Kiindig E.P. Enantioselective synthesis of planar chiral Cr{rf-arene)(CO)3. complexes via nucleophilic addition/hydride abstraction.
574. Preliminary communication. // Helv. Chim. Acta. 1997. — V. 80. — P. 2023−2026
575. Rose-Munch F., Gagliardini V., Renard C., Rose E. (r/6-Arene)tricarbonylchromium and (rf-cyclohexadienyl)tricarbonylmanganese complexes: indirect nucleophilic substitutions. // Coord. Chem. Rev. 1998. — V. 178. — P. 249−268
576. Kiindig E.P., Inage M., Bernardinelli G. Nucleophile/electrophile double additions to (l-methoxynaphthalene)tricarbonylchromium (O). Application in a formal synthesis of the aklavinone ab ring. II Organometallics. 1991. -V. 10.-P. 2921−2930
577. Boutonnet J.C., Rose-Munch F., Rose E., Semra A. Nucleophilic aromatic ipso and tele substitution in the arenetricarbonylchromium series // Bull. Soc. Chim. Fr. 1987. — P. 640−648
578. Rose-Munch F., Aniss K., Rose E. Substitution nucleophile aromatique ipso par des anions d’a-imino-esters ou nitriles sur des fluorobenzenetricarbonylchrome. // J. Organomet. Chem. 1990. — V. 385. -P. C1-C3
579. Rose-Munch F., Khourzom R., Djukic J.P., Perrotey A., Rose E., Brocard J. Reactivite dtialogenobenzene tricarbonylchrome vis-a-vis d’anions de sulfones. Il J. Organomet. Chem. 1994. — V. 467. — P. 195−206
580. Djukic J.P., Rose-Munch F., Rose E., Dromzee Y. Synthesis of tricarbonyl (^5~cyclohexadienyl)chromium complexes via nucleophilic addition of hydride on (? 5-arene)tricarbony lchromium complexes. // J. Amer. Chem. Soc. 1993. — V. 115. — P. 6434−6435
581. Chen W., Sheridan J.B., Cote M.L., Lalancette R.A. Cyclohexa- and cycloheptadienyl complexes of the Group 6 metals. // Organometallics. -1996.-V. 15.-P. 2700−2706
582. Knipe A.C., McGuinness S.J., Watts W.E. Mechanistic features of S-^Ar reactions of neutral and cationic metal-complexed halogenobenzenes with methoxide. // J. Chem. Soc., Chem. Commun. 1979. — P. 842−843
583. Kamikawa K., Kinoshita S., Matsuzaka H., Uemura M. Stereoselective synthesis of axially chiral N-C bonds in yV-aryl indoles. // Org. Lett. -2006.-V. 8.-P. 1097−1100
584. Boutonnet J.-C., Rose-Munch F., Rose E. Highly regioselective aromatic substitution on a diaryloxidetricarbonylchromium complex. // Tetrahedron Lett. 1985. — P. 3989−3992
585. Alemagna A., del Buttero P., Gorini C., Landini D., Licandro E., Maiorana S. SNAr nucleophilic substitutions of Cr (CO)3-complexed aryl halides with thiolates under phase-transfer conditions. // J. Org. Chem. 1983. — V. 48. -P. 605−607
586. Alemagna A., Cremonesi P., del Buttero P., Licandro E., Maiorana S. Nucleophilic aromatic substitution of Cr (CO)3 complexed dihaloarenes with thiolates. // J. Org. Chem. 1983. — V. 48. — P. 3114−3116
587. Baldoli C., del Buttero P., Maiorana S. Aromatic nucleophilic substitution on halogenoarene tricarbonyl chromium complexes: synthesis of Cr (CO)3 complexed aniline derivatives. // Tetrahedron Lett. 1992. — V. 33. — P. 4049−4052
588. Houghton R.P., Voyle M., Price R. Reactions of coordinated ligands: IX. chromium (0)-promoted intramolecularnucleophilic substitution of an aryl halide: a preparation of chroman. // J. Organometal. Chem. 1983. — V. 259.-P. 183−188
589. Rose-Munch F., Khourzom R., Djukic J.-P., Rose E. Reactivite des complexes chlorotrifluoromethylbenzene tricarbonylchrome vis-a-vis d’anions non carbones: Amidure et trifluoroethylate de sodium. // J. Organometal. Chem. 1993. — V. 456. — P. C8-C10
590. Dessey R.E., Pohl R.C., King R.B. Organometallic electrochemistry. VII. The nucleophilicities of metallic and metalloidal anions derived frommetals of Groups IV, V, VI, VII, and VIII. // J. Amer. Chem. Soc. 1966. -V. 88.-P. 5121−5124
591. Semmelhack M.F., Bisaha J., Czarny M. Metalation of arenechromium tricarbonyl complexes and electrophilic trapping of the complexed phenyllithium intermediate. // J. Amer. Chem. Soc. 1979. — V. 101. — P. 768−770
592. Baldoli C., del Buttero P., Maiorana S., Papagni A. Aromatic nucleophilic substitution of Cr (CO)3-complexed halogenoarenes: a new entry to dibenzo crown ethers. // J. Chem. Soc., Chem. Commun. 1985. — P. 1181−1182
593. Rose-Munch F., Rose E., Semra A., Mignon L., Garcia-Oricain J., Knobler C. Substitutions nucleophiles aromatiques SNAr de fluorobenzenetricarbonylchrome. // J. Organometal. Chem. 1989. — V. 363.-P. 297−309
594. Rose-Munch F., Rose E., Semra A. te/e-Substitution in halogenobenzenetricarbonylchromium complexes. // J. Chem. Soc., Chem. Commun. 1987. — P. 942−943
595. Rose-Munch F., Rose E., Semra A., Jeannin Y., Robert F. Substitution nucleophile aromatique cine en serie arenetricarbonylchrome // J. Organometal. Chem. 1988. — V. 353. — P. 53−64
596. Kiindig E.P., Amurrio D., Bernardinelli G., Chowdhury R. Agostic complexes via nucleophile addition/protonation reactions of .5-benzene tris (trifluorophosphine)chromium. // Organometallics. 1993. — V. 12. — P. 4275−4277
597. Persson M., Hacksell U., Csoregh I. Tricarbonylchromium complexes of 2-aminotetralin derivatives. Hydride displacement of aromatic methoxy groups. // J. Chem. Soc., Perkin Trans. 1.- 1991. P. 1453−1459
598. Kiindig E.P., Amurrio D., Liu R., Ripa A. Tricarbonylchromium phenyloxazoline and -imine complexes: Highly regioselective orthoadditions of carbon nucleophiles. // Synlett. 1991. — P. 657−658
599. Hoffmann O., Schmalz H.-G. Electron transfer driven addition of ketimine derived radicals to arene-Cr (CO)3 complexes. // Synlett. 1998. — P. 14 261 428
600. Ohlsson B., Ullenius C. Evidence for reversible attack of a carbanion on an^{6-arenetricarbonylchromium} (0) complex. // J. Organometal. Chem. -1984.-V. 267.-P. C34-C36
601. Semmelhack M.F., Clark G.R., Farina R., Saeman M. Substituent effects in addition of carbanions to arenechromium tricarbonyl complexes: correlation with arene LUMO. // J. Amer. Chem. Soc. 1979. — V. 101. -P. 217−218
602. Semmelhack M.F., Schmalz H.-G. Asymmetric induction in the nucleophile addition to^{6-arene-tricarbonyl-chromium} (0) complexes. // Tetrahedron Lett. 1996. — V. 37. — P. 3089−3092
603. Kiindig E.P., Desobry V., Simmons D.P. Regioselectivity in the addition of carbanions to (l, 4-dimethoxynaphthalene)tricarbonylchromium. A new entry into anthracyclinone synthesis. // J. Amer. Chem. Soc. 1983. — V. 105.-P. 6962−6963
604. Pfletschinger A., Koch W., Schmalz H.-G. On the regioselectivity of nucleophilic additions to anisole-Cr (CO)3 and related complexes: a density functional study. // New J. Chem. 2001. — V. 25. — P. 446−450
605. Albright T.A., Carpenter B.K. Conformational effects of nucleophilic and electrophilic attack on (arene)chromium tricarbonyl complexes. // Inorg. Chem. 1980. — V. 19. — P. 3092−3097
606. Albright T.A., Hofmann P., Hoffmann R. Conformational preferences and rotational barriers in polyene-ML3 transition metal complexes. // J. Amer. Chem. Soc. 1977. — V. 99. — P. 7546−7557
607. Semmelhack M.F., Yamashita A. Arene-metal complexes in organic synthesis: synthesis of acorenone and acorenone B. // J. Amer. Chem. Soc.- 1980. V. 102. — P. 5924−5926
608. Semmelhack M.F., Harrison J.J., Thebtaranonth Y. Formation of 3-substituted cyclohexenones by nucleophilic addition to anisole-chromium complexes. // J. Org. Chem. 1979. — V. 44. — P. 3275−3277
609. Pearson A.J., Gontcharov A.V. Asymmetric conversion of arenechromium complexes to functionalized cyclohexenones: Progress toward defining an optimum chiral auxiliary. // J. Org. Chem. 1998. — V. 63. — P. 152−162
610. Kundig E.P., Simmons D.P. The transformation of arenes into acetyl dienes via nucleophilic addition to arene-Cr (CO)3 complexes and trapping with Mel. // J. Chem. Soc., Chem. Commun. 1983. — P. 1320−1322
611. Collman J.P. Disodium tetracarbonylferrate, a transition metal analog of a Grignard reagent. // Acc. Chem. Res. 1975. — V. 8. — P. 342−347
612. Semmelhack M.F., Seufert W., Keller L. Arene-metal complexes in organic synthesis: Addition to styrene-type ligands. //J. Amer. Chem. Soc. 1980. — V. 102. — P. 6584−6586
613. Bach T. Additions to functionalized arenes with concurrent dearomatization. // Angew. Chem., Int. Ed. Engl. 1996. — V. 35. — P. 729 730
614. Pearson A.J., Paramahamsan H., Dudones J.D. Vicinal stereocontrol during nucleophilic addition to arene chromium tricarbonyl complexes:? Formal synthesis of {±)-erythro juvabione. // Org. Lett. 2004. — V. 6. — P. 21 212 124
615. Kamikawa K., Shimizu Y., Matsuzaka H., Uemura M. Stereoselective 3+2+2. 'cycloaddition utilizing optically active binuclear Fischer carbene complexes with alkynes.// J. Organomet. Chem. 2005. — V. 690. — P. 5922−5928
616. Herberich G.E., Fischer E.O. Uber Aromatenkomplexe von Metallen, LXV. Die Isomerenverteilung bei der Friedel-Crafts-Acetylierung des n-Toluol-chrom-tricarbonyls und des freien Toluols. // Chem. Ber. 1962. -V. 95, — P. 2803−2809
617. Brown D.A., Raju J.R. Molecular-orbital theory of organometallic compounds. Part VI. Substitution reactions of some tricarbonylarenechromiums. // J. Chem. Soc. A. 1966. — P. 40−43
618. Brown D.A. Hughes F.J. Electrophilic substitution reactions of tricarbonylarenemetals. // Inorg. Chim. Acta. 1967. — V. 1. — P. 448−450
619. Gracey D.E.F., Jackson W.R., Jennings W.B. The acetylation of tricarbonyl-(/ram-1,3-dimethylindane)chromium. // J. Chem. Soc., Chem. Commun. 1968. — P. 366−367
620. Jackson W.R., Jennings W.B. The stereochemistry of organometallic compounds. Part VII. Acetylation of sometricarbonyl (alkylbenzene)chromium compounds. // J. Chem. Soc. B. -1969.-P. 1221−1228
621. Rosea S., Chiraleu F., Rosea S.I. Electrophilic aromatic-substitution in arene-tricarbonyl-chromium complexes. // Rev. Roum. Chim. 1991. — V. 36.-P. 693−705
622. Merlic C.A., Miller M.M. Neighboring group participation by chromium in substitution reactions of (^6-arene)tricarbonylchromium complexes. // Organometallics. 2001. — V. 20. — P. 373−375
623. Магомедов Г. К.-И., Сыркин В. Г., Френкель A.C. Меркурирование бензолхромтрикарбонила. // Ж. общей химии. 1972. — Т. 42. — С. 2450−2452
624. Magomedov G.K.-I. Metal carbonyls: new methods of synthesis and investigations. // J. Organomet. Chem. 1990. — V. 385. — P. 113−130 •
625. Berger A., de Cian A., Djukic J.-P., Fischer J., Pfeffer M. Syntheses of ortho-mercurated and -palladated (^6-arene)tricarbonylchromium complexes. // Organometallics. 2001. — V. 20. — P. 3230−3240
626. Магомедов Г. К.-И., Сыркин В. Г., Френкель A.C., Некрасов Ю. С., Завина Т. А. Меркурирование аренхромтрикарбонилов и бензолхромдикар-бонилтрифенилфосфина // Ж. общей химии. 1975. -Т. 45.-С. 2533−2536
627. Graddon D.P., Gregor I.K., Siddiqi I.A. Stability and bond strength in adducts of mercury (II) halides with transition metal carbonyl derivatives. // J. Organomet. Chem. 1975. — V. 102. — P. 321−326
628. Raush M.D., Gloth R.E. The formation and some reactions of rf-phenyllithiumtricarbonylchromium. // J. Organometal. Chem. 1978. — V. 153.-P. 59−66
629. Streitwieser A., Jr., Boerth D.W. Carbon acidity. 54. Kinetic acidities of cycloalkenes with lithium cyclohexylamide. // J. Amer. Chem. Soc. 1978. -V. 100.-P. 755−759
630. Uemura M., Nishikawa N., Hayashi Y. Regioselective lithiation of rf-(arene)chromium tricarbonyl complexes. // Tetrahedron Lett. 1980. — V. 21.-P. 2069−2072
631. Gibson S.E., Guillo N., White A.J.P., Williams D.J. A reactivity study of ^6-(/eri-butylsulfonyl)benzene.-tricarbonylchromium (0). // J. Chem. Soc. Perkin Trans. 1. 1996. — P. 2575−2581
632. Gschwend H.W., Rodriguez H.R. Heteroatom-facilitated lithiations. // Org. React.- 1979.-V. 26.-P. 1−360
633. Gilman H., Soddy T. Metalation of aryl fluorides in tetrahydrofuran. // J. Org. Chem. 1957,-V. 22.-P. 1715−1716
634. Нефедов O.M., Дьяченко А. И. Исследование стабильности о-галоидлитийбензолов предшественников дегидробензола в различных растворителях // Докл. АН СССР. — 1971. — Т. 198. — С. 593−596
635. Semmelhack M.F., Ullenius C. On the stability and decomposition of rj6-(2-lithiochlorobenzene)tricarbonylchromium (O). // J. Organomet. Chem. -1982.-V. 235.-P. C10-C12
636. Fukui M., Ikeda T., Oishi T. Meta functionalization of anilines and phenol. // Tetrahedron Lett. 1982. — V. 23. — P. 1605−1608
637. Fukui M., Ikeda T., Oishi T. Meta functionalization of anilines and phenol. // Chem. Pharm. Bull. 1983. — V. 31. — P. 466−475
638. Masters N.F., Widdowson D.A. Regiocontrolled lithiation of arenetricarbonylchromium (O) complexes: meta-substitution of phenols and anilines. // J. Chem. Soc. Chem. Commun. 1983. — P. 955−956
639. Clough J.M. Steric and electronic perturbations of triisopropylsiloxy directed lithiations in arenetricarbonylchromium ((J) complexes. // Synlett -1990.-P. 469−470
640. Koide H., Hata T., Yoshihara K., Kamikawa K., Uemura M. Asymmetric synthesis of axially chiral benzamides and anilides utilizing planar chiral arene chromium complexes. // Tetrahedron. 2004. — V. 60. — P. 45 274 541
641. Kamikawa K., Watanabe T., Uemura M. Stereoselective synthesis of both enantiomers of axially chiral biaryls utilizing planar chiral tricarbonyl (arene)chromium complexes. // J. Org. Chem. 1996. — V. 61. -P. 1375−1384
642. Watanabe T., Shakadou M., Uemura M. Diastereoselective orf/zo-lithiation of tricarbonylchromium complexes of chiral benzaldehyde acetals. // Inorg. Chim. Acta. 1999. — V. 296. — P. 80−85
643. Watanabe T., Shakadou M., Uemura M. Stereoselective synthesis of korupensamine A and e"/-korupensamine B utilizing and identical planar chiral arene chromium complex. // Synlett. 2000. — P. 1141−1144
644. Michon C., Murai M., Nakatsu M., Uenishi J., Uemura M. Regiochemical observations depending on electrophiles in directed lithiation of 1,3-diheteroatom substituted arene tricarbonylchromium complexes. // Tetrahedron. 2009. — V. 65. — P. 752−756
645. Michon C., Liu S., Hiragushi S., Uenishi J., Uemura M. Gold (I)-catalyzed cycloisomerization of (arene)chromium complexes with enyne bonds directed towards axially chiral biaryls. // Synlett. 2008. — P. 1321−1324
646. Moser W.H., Endsley K.E., Colyer J.T. Stereoselective bis-functionalizations of arene chromium tricarbonyl complexes via Brook rearrangements. // Org. Lett. 2000. — V. 2. — P. 717−719
647. Quattropani A., Bernardinelli G., Kundig E.P. Enantioselective deprotonation/electrophile addition reactions of tricarbonyl (phenyl carbamate) chromium complexes. // Helv. Chim. Acta. 1999. — V. 82. — P. 90−104
648. Gilday J.P., Widdowson D.A. Lithiation of 2-, 3-, and 4-fluoroanisole (tricarbonyl)chromium (0) complexes: a reversal of normal regiocontrol. //J. Chem. Soc., Chem. Commun.- 1986. P. 1235−1237
649. Gilday J.P., Negri J.T., Widdowson D.A. A novel order of ortho-directing abilities in the lithiation of^{6-arenetricarbonylchromium} (0) complexes. // Tetrahedron. 1989. — V. 45. — P. 4605−4618
650. Dickens P.J., Gilday J.P., Negri J.T., Widdowson D.A. Chromium directed regio- and stereocontrol: A new chapter in aromatic natural product synthesis. // Pure Appl. Chem. 1990. — V. 62. — P. 575−581
651. Treichel P.M., Kirss R.U. Metalation of the fused polycyclic aromatic ligand in (arene)chromium tricarbonyl complexes: kinetic and thermodynamic site preferences. // Organometallics. 1987. — V. 6. — P. 249−254
652. Kirss R.U., Treichel P.M. Haptotropic rearrangements in naphthalene-chromium tricarbonyl complexes. // J. Amer. Chem. Soc. 1986. — V. 108. -P. 853−855
653. Kiindig E.P., Grivet C., Spichiger S. Reversibility of the lithiation of rf-naphthalenetricarbonylchromium. // J. Organomet. Chem. 1987. — V. 332. -P. C13-C16
654. Masters N.F., Mathews N., Nechvatal G., Widdowson D.A. /?en-Directed 7-substitution in 776-indoletricarbonylchromium(0) complexes. // Tetrahedron. 1989. — V. 45. — P. 5955−5970
655. Nechvatal G., Widdowson D.A. A new synthesis of 4-substitued indoles via tricarbonylarenechromium (O) complexes. // J. Chem. Soc., Chem. Commun. 1982. — P. 467−468
656. Beswick P.J., Greenwood C.S., Mowlem T.J., Nechvatal G., Widdowson D.A. The synthesis of 4-substituted indoles via arenetricarbonylchromium (O) complexes. // Tetrahedron. 1988. — V. 44. -P. 7325−7334
657. Gilday J.P., Widdowson D.A. Flourine directed lithiation in tricarbonylarenechromium (O) complexes: The regiospecific synthesis of polysubstituted arenes. // Tetrahedron Lett. 1986. — V. 27. — P. 5525−5528
658. Beswick P.J., Widdowson D.A. The synthesis of 3-methylene-2,3-dihydrobenzofuran stabilised as its tricarbonylchromium complex // Synthesis. 1985. — P. 492−493
659. Silverthorn W.E. Arene transition metal chemistry. // Adv. Organometal. Chem. 1975.-V. 13.-P. 47−137
660. Price D.A., Simpkins N.S., MacLeod A.M., Watt A.P. Chiral basemediated asymmetric synthesis of tricarbonyl (?5-arene)chromium complexes. // J. Org. Chem. 1994. — V. 59. — P. 1961−1962
661. Krizan T.D., Martin J.C. In situ trapping of ortho lithiated benzenes containing electrophilic directing groups. // J. Amer. Chem. Soc. 1983. -V. 105.-P. 6155−6157
662. Rose-Munch F., Rose E., Semra A. Substitution nucleophile aromatique cine d’un groupe methoxy en serie arenetricarbonylchrome. // J. Organomet. Chem. 1989. — V. 377. — P. C9-C12
663. Davies S.G., Loveridge T., Clough J.M. Regioselective ortho substitution of diphenyl sulfoxide chromium tricarbonyl: complementary stereoselectivities for the mono- and di-anions. // J. Chem. Soc., Chem. Commun. 1995.-P. 817−818
664. Schmaltz H.G., Volk T., Bernicke D. On the deprotonation of rf-1,3-dimethoxybenzene-Cr (CO)3 derivatives: Influence of the reaction conditions on the regioselectivity. // Tetrahedron. 1997. — V. 53. — P. 9219−9232
665. Ariffin A., Blake A.J., Ewin R.A., Li W.-S., Simpkins N.S. The asymmetric synthesis of phosphorus- and sulfur-containing tricarbonyl (^6-arene)chromium complexes using the chiral base approach. // J. Chem. Soc. Perkin Trans. 7. 1999. — P. 3177−3189
666. Gibson S.E., Saladin S.A., Sur S. Unusual insubstitutions on {rf-arene)tricarbonylchromium (O) complexes and evidence for the formation of a tri anion. // J. Chem. Soc., Chem. Commun. 2000. — P. 2011−2012
667. Kiindig E.P., Quattropani A. Planar chiral arene tricarbonylchromium complexes via enantioselective deprotonation/electrophile addition reactions. // Tetrahedron Lett. 1994. — V. 35. — P. 3497−3500
668. Ewin R.A., MacLeod A.M., Price D.A., Simpkins N.S., Watt A.P. Chiral base mediated asymmetric synthesis of tricarbonyl (^<5-arene)chromium complexes. // J. Chem. Soc. Perkin Trans. 1. 1997. — P. 401−416
669. Wright M.E. Chemistry of ?5-bis (tri-«-butylstannyl)benzene.chromium tricarbonyl complexes. Versatile intermediates in the preparation of substituted (? 5-arene)chromium tricarbonyl systems. // Organometallics. -1989.-V. 8.-P. 407−411
670. Jaouen G. The effect of transition metal benzyl and propargyl species on the behavior of steroidal hormones. // Pure Appl. Chem. 1986. — V. 58. -P. 597−616
671. Olah G.A., Yu S.H. Organometallic chemistry. 9. Carbon-13 nuclear magnetic resonance study of the cumylchromium tricarbonyl and of cycloheptatrienylmolybdenum (-chromium, and -tungsten) tricarbonyl cations. //J. Org. Chem. 1976. -V. 41. — P. 1694−1697
672. Acampora M., Ceccon A., dal Farm M., Giacometti G., Rigatti G. Carbon-13 nuclear magnetic resonance spectra of 1-p-tolylethyl- and di-p-tolylmethyl-tricarbonylchromium cations. // J. Chem. Soc., Perkin Trans. 2. 1977.-P. 483−486
673. Seyferth D., Merola J.S., Eschbach C.S. Metal-stabilized carbonium ions derived from bis (tricarbonylchromium) complexes of diarylmethanes. // J. Amer. Chem. Soc. 1978.-V. 100.-P. 4124−4131
674. Downton P.A., Sayer B.G., McGlinchey MJ. Carbon-13 NMR spectroscopic and EHMO study of slowed tripodal rotation in (benzyl)Cr (CO)3.+ and (fulvene)Cr (CO)3 systems: metal-stabilized nonplanar cations. // Organometallics. 1992. — V. 11. — P. 3281−3286
675. Netz A., Drees M., Strassner T., Miiller T.J.J. Planar chiral (arene)chromiumcarbonyl-substituted propargyl cations. A spectroscopic and computational study. // Eur. J. Org. Chem. — 2007. — P. 540−547
676. Solladie-Cavallo A. Arene-chromium tricarbonyl complexes: Bonding and behaviour. // Polyhedron. 1985. — V. 4. — P. 901−927
677. Solladie-Cavallo A. Chiral arene-chromium-carbonyl complexes in asymmetric synthesis. // In: Advances in Metal-Organic Chemistry. — Liebeskind L.S. (Ed.). JAI Press. — Greenwich. — 1989. — V. 1. — P. 99 133
678. Davies S.G., Coote S.J., Goodfellow C.L. Synthetic applications of chromium tricarbonyl stabilized benzylic carbanions // In: Advances in Metal-Organic Chemistry. -Liebeskind L.S. (Ed.). JAI Press. — London. -1991.-V. 2.-P. 1−57
679. Uemura M. Tricarbony 1(^/5-arene)chromium complexes in organic synthesis. // In: Advances in Metal-Organic Chemistry. -Liebeskind L.S. (Ed.). JAI Press. — London. — 1991. -V. 2. — P. 195−245
680. Davies S.G., Donohoe T.J. Arene chromium tricarbonyl stabilised benzylic carbocations. // Synlett. 1993. — P. 323−332
681. Davies S.G., Donohoe T.J., Williams J.M.J. Stereoselective manipulation of acetals derived from o-substituted benzaldehyde chromium tricarbonyl complexes. // Pure Appl. Chem. 1992. — V. 64. — P. 379−386
682. Davies S.G. Stereocontrolled synthesis of iV-methy 1−1,2,3,4-tetrahydroisoquinoline derivatives via chromium tricarbonyl methodologies. // J. Organometal. Chem. 1990. — V. 400. — P. 223−234
683. Terrier F., Farrell P.G., Lelievre J., Top S., Jaouen G. Relative acidifying effects of tricarbonylchromium (O) and /?-nitro groups upon di- and triphenylmethanes. // Organometallics. 1985. — V. 4. — P. 1291−1296
684. Ceccon A., Gambaro A., Venzo A. Metal-stabilized carbanions: VI. Formation of some arylmethyl and dibenzotropenyl carbanions complexedwith tricarbonylchromium. A kinetic and a 13C NMR study. // J. Organometal. Chem. 1984. — V. 275. — P. 209−222
685. Lebibi J., Brocard J., Couturier D. Reactivities of tricarbonylchromiumarenes reaction with carbonyl-compounds // Bull. Soc. Chim. Fr., Part. II. — 1982. — P. 357−361
686. Beswick P.J., Leach S.J., Masters N.F., Widdowson D.A. Synthetic applications of lithiated tricarbonyl-^-arenechromium (O) complexes: Copper and palladium catalysed substitutions. // J. Chem. Soc., Chem. Commun. 1984. — P. 46−48
687. Ceccon A., Piccini F., Venzo A. Organometallic carbanions. Attempted metalation of arylmethanes complexed with tricarbonylchromium // Gazz. Chim. Ital. 1978. — V. 108. — P. 705−706
688. Jaouen G. Examples of the use of chromium tricarbonyl-arene complexes in organic synthesis. // Ann. N. Y. Acad. Sci. 1977. — V. 295. — P. 59−78
689. Simonneaux G., Jaouen G. Alkylation selective de substituants aromatiques actives par un greffon chrome carbonyle. // Tetrahedron. -1979. V. 35. — P. 2249−2254
690. Brocard J., Lebibi J., Couturier D. Benzylic functionalization of arene (tricarbonyl)chromium complexes. // J. Chem. Soc., Chem. Commun. 1981. — P. 1264−1265
691. Caro B., Le Bihan J.-Y., Guillot J.-P., Top S., Jaouen G. Synthesis of ethyl phenylpyruvate and related compounds using chromium tricarbonyl complexes. // J. Chem. Soc., Chem. Commun. 1984. — P. 602−603
692. Senechal D., Senechal-Tocquer M.-C., Gentric D., Le Bihan J.-Y., Caro B., Gruselle M., Jaouen G. Synthesis of oximes from (arene)Cr (CO)3 complexes by nitrosation at the benzylic position. // J. Chem. Soc., Chem. Commun. 1987. — P. 632−633
693. Gentric D., Le Bihan J.-Y., Senechal-Tocquer M-C., Senechal D., Caro B. Comportement des allylbenzenes chrometricarbonyle en milieu basique. // Tetrahedron Lett. 1986. — V. 27. — P. 3849−3852
694. Traylor T.G., Goldberg M.J. Neighboring group participation in organometallic chemistry. Internal exchange in (diarylalkane)tricarbonylchromium complexes. // J. Amer. Chem. Soc. -1987. -V. 109. P. 3968−3973
695. Brocard J., Lebibi J. Fonctionnalisation benzylique en serie arene chrome tricarbonyle. Controle electronique de la regiospecificite de la reaction. // J. Organometal. Chem. 1987. — V. 320. — P. 295−306
696. Brocard J., Laconi A., Couturier D., Top S., Jaouen G. Substituent effects in benzylic functionalization of arene (tricarbonyl) chromium complexes. // J. Chem. Soc., Chem. Commun. 1984. — P. 475−476
697. Jaouen G., Top S., Laconi A., Couturier D., Brocard J. Regiospecific and stereospecific functionalization of benzylic sites by tricarbonylchromium arene complexation. // J. Amer. Chem. Soc. 1984. — V. 106. — P. 22 072 208
698. Brocard J., Lebibi J. Reaction diastereoselective de carbanions issus d’arenes chrome tricarbonyle. // J. Organometal. Chem. 1986. — V. 310. -P. C63
699. Blagg J., Davies S.G. The highly stereoselective conversion of N, N-dimethylamphetamine into TV-methylpseudoephedrine- A mimic of theenzyme mediated stereospecific benzylic H. // Tetrahedron. 1987. — V. 43.-P. 4463−4471
700. Brocard J., Mahmoudi M., Pelinski L., Maciejewski L. Transposition 2, 3. de Wittig diastereospecifique en serie arene chrome tricarbonyle. // Tetrahedron Lett. 1989. — V. 30. — P. 2549−2552
701. Top S., Vessieres A., Abjean J.-P., Jaouen G. Stereospecific 6-alkylation of oestradiol derivatives via Cr (CO)3 complexes. // J. Chem. Soc., Chem. Commun. 1984. — P. 428−429
702. Kiinzer H., Thiel M. A novel route to 3-alkylated estra-1,3,5(lO)-trienes. // Tetrahedron Lett. 1988. — V. 29. — P. 1135−1136
703. Gill J.C., Marples B.A., Traynor J.R. Regioselective 2-hydroxylation of 3-methoxyoestra-l, 3,5(10)-trienes via chromium carbonyl complexes. // Tetrahedron Lett. 1987. — V. 28. — P. 2643−2644
704. Arzeno H.B., Barton D.H.R., Davies S.G., Lusinchi X., Meunier B., Pascard C. Synthese de la 10(iS)-methyl-codeine et de la 10(S)-methyl-morphine. // Nouv. J. Chim. 1980. — V. 4. — P. 369−375
705. Mathews N., Sainsbury M. Stereoselective alkylation of a codeine if-chromium tricarbonyl complex. // J. Chem. Res. (S). 1988. P. 82−83
706. Davies S.G. Stereoselective synthesis via arene chromium tricarbonyl complexes. // Chem. Ind. 1986. — P. 506−509
707. Baird P.D., Blagg J., Davies S.G., Sutton K.H. The stereospecific synthesis of (-)-(8#) and (-)-(8"S)-methylcanadine. // Tetrahedron. 1988. — V. 44. -P. 171−186
708. Lebibi J., Pelinski L., Maciejewski L., Brocard J. Hydroxymethylation enantioselective d’alkyl benzenes chrome tricarbonyle ortho substitutes. // Tetrahedron. 1990. — V. 46. — P. 6011−6020
709. Lenhi A., Lavergne J.-P., Viallefont Ph. Syntheses de /?-et (5-aryl a-amino esters: reactions d’anions benzyliques chrome tricarbonyle sur des halogeno a-amino esters // J. Organometal. Chem. 1991. — V. 401. — P. Cl4-C16
710. Solladie-Cavallo A., Farkhani D. Enantioselective synthesis of chiral benzylic amines. (A stereospecific transamination-alkylation reaction). // Tetrahedron Lett. 1986. — V. 27. — P. 1331−1334
711. Uemura M., Nishimura H., Hayashi Y. (^6-Arene)chromium complexes in organic synthesis: 2,3.-Wittig rearrangement of (benzyl crotyl ether) chromium complexes. // J. Organometal. Chem. 1989. — V. 376. -P. C3-C6
712. Mahmoudi M., Pelinski L., Maciejewski L., Brocard J. Transportation (2,3) de Wittig des ethers d’allyle ou crotyle et de benzyle chrome tricarbonyle. // J. Organometal. Chem. 1991. — V. 405. — P. 93−99
713. Uemura M., Nishimura H., Minami T., Hayashi Y. (?Arene)chromium complexes in organic synthesis: synthesis of (±)-dihydroxyserrulatic acid. // J. Amer. Chem. Soc. 1991. — V. 113. — P. 5402−5410
714. Uemura M., Minami T., Hayashi Y. Synthesis of 11-deoxyanthracyclinone via (arene)tricarbonylchromium complexes. // J. Chem. Soc., Chem. Commun. 1984. — P. 1193−1194
715. Jackson W.R., Mitchell T.R.B. The stereochemistry of organometallic compounds. Part VIII. Stereochemistry of reduction of some tricarbonyl (arylcycloalkanone)-chromiums. //J. Chem. Soc. (B). 1969. -P. 1228−1230
716. Jaouen G., Meyer A. Some facile syntheses of optically active 2-substituted indanones, indanols, tetralones, and tetralols via their chromium tricarbonyl complexes.// J. Amer. Chem. Soc. 1975. — V. 97. — P. 4667−4672
717. Uemura M., Take K., Hayashi Y. Regioselective synthesis of anthraquinones via (arene)chromium tricarbonyl complexes. // J. Chem. Soc., Chem. Commun. 1983. — P. 858−859
718. Uemura M., Isobe K., Hayashi Y. Stereo- and regioselective synthesis of hydroxycalamenenes via (arene)tricarbonyl chromium complexes. // Chem. Lett. 1985. — V. 14. — P. 91−94
719. Uemura M., Isobe K., Take K., Hayashi Y. (Arene)chromium tricarbonyl complexes in organic synthesis: stereoselective synthesis of eis- and trans -7-hydroxycalamenenes. // J. Org. Chem. 1983. — V. 48. — P. 3855−3858
720. Hart T.W., Vacher B. Versatile intramolecular reactions starting from a conformationally restricted epoxyalcohol. // Tetrahedron Lett. 1978. — V. 33.-P. 3009−3012
721. Caro B., Jaouen G. Reduction par le borohydrure de sodium d’indanones chrome tricarbonyle exo substituees en a et /? position de l’etat de transition et facteurs. // Tetrahedron. 1983. — V. 39. — P. 83−92
722. Caro B., Jaouen G. Reduction par le borohydrure de sodium d’indanones chrome tricarbonyle endo substituees en «et y? position de l’etat de transition et facteurs. // Tetrahedron. 1983. — V. 39. — P. 93−102
723. Jaouen G., Dabard R. Utilisation des derives du benzene chrome tricarbonyle comme intermediaires de synthese en serie benzenique. // Tetrahedron Lett.-1971.-V. 12.-P. 1015−1018
724. Top S., Meyer A., Jaouen G. Stereoselective nucleophilic attacks on carbenium ions generated from (1-indanol) — and (l-tetralol)Cr (CO)3 as synthetic intermediates. // Tetrahedron Lett. 1979. — V. 20. — P. 35 373 540
725. Wey H.G., Butenschon H. Ring opening of a cyclobutabenzene complex under very mild conditions. // Angew. Chem. Int. Ed. Engl. 1991. — V. 30.-P. 880−881
726. Brands M., Wey H.G., Butenschon H. Unexpected proximal ring opening reactions of benzocyclobutene complexes. // J. Chem. Soc., Chem. Commun.-1991.-P. 1541−1542
727. Uemura M., Isobe K., Hayashi Y. (r|6-Arene)tricarbonylchromium complex in organic synthesis: stereoselective alkylation at benzylic positionof (^-arene) tricarbonylchromium. // Tetrahedron Lett. 1985. — V. 26. -P. 767−770
728. Uemura M., Kobayashi T., Hayashi Y. (^6-Arene)-tricarbonylchromium complexes in organic synthesis: Stereoselective carbon-carbon bond formation via (?/6-arene)-tricarbonylchromium carbocations. // Synthesis. -1986.-P. 386−388
729. Meyer A., Dabard R. Exemples d’induction asymetrique en serie du benchrotrene // J. Organometal. Chem. 1972. — V. 36. — P. C38-C42
730. Besancon J., Tirouflet J., Card A., Dusausoy Y. Recherches dans la serie des metallocenes: XXVIII. Action des rectifs de grignard sur les cetones benchrotreniques chirales. // J. Organometal. Chem. 1973. — V. 59. — P. 267−279
731. Solladie-Cavallo A., Suffert J. Synthesis of (+)-S-a-perfluoroethyl-a-hydroxyphenyl acetic acid and highly effective auxiliaries for use in asymmetric induction. // Tetrahedron Lett. 1984. — V. 5. — P. 1897−1900
732. Solladie-Cavallo A., Suffert J. Synthesis of optically pure perfluoroalkyl aryl carbinols. // Synthesis. 1985. — P. 659−662
733. Solladie-Cavallo A., Quazzotti S. l, l-Dichloro-2,2,2-trifluoroethyllithium in asymmetric synthesis, II. A route to optically pure 4,4,4-trifluoro-2-hydroxybutanoic acid. // Synthesis. 1991. — P. 177−180
734. Davies S.G., Goodfellow C.L. Asymmetric synthesis of a-substituted benzyl alcohols via the stereoselective addition of nucleophiles to homochiral tricarbonyl (^6-o-triisopropylsilylbenzaldehyde)chromium (0). // Synlett. 1989. — P. 59−62
735. Baldoli C., del Buttero P. Arenetricarbonylchromium complexes as chiral auxiliaries: asymmetric synthesis of /^-lactams. // J. Chem. Soc., Chem. Commun. 1991. — P. 982−984
736. Kiindig E.P., Long H.X., Romanens P., Bernardinelli G. Highly diastereoselective coupling reactions between chiral benzaldehyde tricarbonylchromium complexes and activated double bonds. // Tetrahedron Lett. 1993. — V. 34. — P. 7049−7052
737. Mukai C., Won J.C., In J.K., Hanaoka M. Tricarbonyl (benzaldehyde)-chromium (O) complexes in organic synthesis: A highly stereoselective 1,3-dipolar cycloaddition of chromium (0)-complexed nitrones. // Tetrahedron Lett. 1990.-V. 31.-P. 6893−6896
738. Besancon J., Card A., Dusausoy Y., Tirouflet J. Action of Grignard reagents on chiral benchrotrene ketones. // C. R. Acad. Sci. Paris, Ser. C. -1972.-V. 274.-P. 545−548
739. Besancon J., Tirouflet J. Recherches dans la serie des metallocenes. XIII. Derives du chrome tricarbonyle: problemes d’induction asymetrique et de configuration absolue. // Bull. Soc. Chim. France. -1969.-No. 3.-P. 861−870
740. Uemura M., Minami T., Shiro M., Hayashi Y. Transformations of chiral (?6-arene)chromium complexes in organic synthesis: aldol reactions of (ortho-substituted acetophenone) chromium. // J. Org. Chem. 1992. — V. 57.-P. 5590−5596
741. Uemura M., Minami T., Hayashi Y. Diastereoselective aldol reaction of 07o-X-C6H4COCH3)Cr (CO)2L complexes. // Tetrahedron Lett. 1989. — V. 30.-P. 6383−6386
742. Uemura M., Minami T., Hayashi Y. (^o-Arene)tricarbonyl chromium complexes in organic synthesis 1,5-remote diastereoselection. // Tetrahedron Lett. 1988. — V. 29. — P. 6271−6274
743. Uemura M., Minami T., Hayashi Y. Diastereoselective Cr (CO)3 complexation of arene compounds mediated by a remote hydroxy 1 group. // J. Amer. Chem. Soc. 1987. — V. 109. — P. 5277−5278
744. Uemura M., Minami T., Hirotsu K., Hayashi Y. 1,5-Stereocontrol via (n5-arene)tricarbonylchromium complexes. // J. Org. Chem. 1989. — V. 54. -P. 469−477
745. Schlogl K. Stereochemistry of Metallocenes. // Top. Stereochem. 1967. -V. l.-P. 39−91
746. Collman J. P., Hegedus L. S., Norton J. R., Finke R. G. Synthetic applications of arene transitionmetal complexes. // In: Principles and applications of organotransition metal chemistry. — University Science Books. Mill Valley. — CA. — 1987. — P. 921
747. Tanaka K., Watanabe T., Shimamoto K.-Y., Sahakipichan P., Fuji K. Asymmetric olefination of metallic arene or diene complexes to form planar chiral complexes. // Tetrahedron Lett. 1999. — V. 40. — P. 65 996 602
748. Villani C., Pirkle W.H. Direct high-performance liquid chromatographic resolution of planar chiral tricarbonyl (^6-arene)-chromium (0) complexes. // J. Chromatogr. A. 1995. — V. 693. — P. 63−68
749. Fukuzawa S., Kato H., Ohtaguchi M., Hayashi Y., Yamazaki H. Preparation of chiral tricarbonyl arene thiol chromium and its application to asymmetric ring opening of meso-epoxides. // J. Chem. Soc., Perkin Trans. 7.- 1997.-P. 3059−3064
750. Kundig E.P., Amurrio D., Anderson G., Beruben D., Khan K., Ripa A., Ronggang L. Chiral auxiliaries, ligands and arene chromium complexes. // Pure Appl. Chem. 1997. — V. 69. — P. 543−546
751. Schelhaas K., Schmalz H.-G., Bats J.W. Chiral^6-arene-Cr (CO)3. complexes as synthetic building blocks: A short enantioselective total synthesis of (+)-ptilocaulin. // Chem. Eur. J. 1998. — V. 4. — P. 57−66
752. Son S.U., Jang H.-Y., Lee I.S., Chung Y.K. Synthesis of planar chiral (1,2-disubstituted arene) chromium tricarbonyl compounds and their application in asymmetric hydroboration. // Organometallics. 1998. — V. 17. — P. 3236−3239
753. Son S.U., Jang H.-Y., Han J.W., Lee I.S., Chung Y.K. New planar chiral P. AMigands containing tricarbonyl (arene)chromium for enantioselective asymmetric hydroboration of styrenes. // Tetrahedron: Asymmetry. 1999. -V. 10.-P. 347−354
754. Jones G.B., Guzel M., Heaton S.B. Enantioselective catalysis using planar chiral^-arene chromium complexes: 1,2-diols as cycloaddition catalysts. // Tetrahedron: Asymmetry. 2000. — V. 11. — P. 4303−4320
755. Koide H., Uemura M. Synthesis of axially chiral benzamides utilizing tricarbonyl (arene)chromium complexes. // Chirality. 2000. — V. 12. — P. 352−359
756. Kondo Y., Green J.R., Ho J. The asymmetric metalation of chiral arylaldehyde acetal chromium tricarbonyl complexes. // J. Org. Chem. -1991.-V. 56.-P. 7199−7201
757. Aube J., Heppert J.A., Milligan M.L., Smith M.J., Zenk P. Asymmetric deprotonation and complexation reactions mediated by chiral ketals as a route to ortho-disubstituted (?5-arene)Cr (CO)3 complexes. // J. Org. Chem.- 1992. V. 57. — P. 3563−3570
758. Han J.W., Son S.U., Chung Y.K. Chiral auxiliary-directed asymmetric ori/zo-lithiation of (arene)tricarbonylchromium complexes. // J. Org. Chem.- 1997. V. 62. — P. 8264−8267
759. Coote S.J., Davies S.G., Goodfellow C.L., Sutton K.H., Middlemiss D., Naylor A. Tricarbonylchromium (O) promoted stereoselective transformations of ephedrine and pseudoephedrine derivatives. // Tetrahedron: Asymmetry. 1990. -V. 1. — P. 817−842
760. Alexakis A., Kanger T., Mangeney P., Rose-Munch F., Perrotey A., Rose E. Enantioselective ortho-lithiation of benzaldehyde chromiumtricarbonyl complex. // Tetrahedron: Asymmetry. 1995. V. 6. — P. 2135−2138
761. Alexakis A., Kanger T., Mangeney P., Rose-Munch F., Perrotey A., Rose E. Enantioselective ori/zo-lithiation of aminals of benzaldehyde chromiumtricarbonyl complex. // Tetrahedron: Asymmetry. 1995. — V. 6. -P. 47−50
762. Davies S.G., Hume W.E. Asymmetric synthesis of the enantiomers of the diary lcarbinol (li?) — and (1 S)-1-(1 -hydroxyphenylmethy l)-2-hydroxybenzene. // J. Chem. Soc., Chem. Commun. 1995. — P. 251−252
763. Bolm C., Muniz K., Ganter C. New chiral tricarbonyl (/-arene)chromium (O) complexes: synthesis and preliminary application in asymmetric catalysis. // New J. Chem. 1998. — P. 1371−1376
764. Siwek M.J., Green J.R. (.R) — and (^-enantioselective lithiation of (arene)tricarbonylchromium acetal complexes with chiral alkyllithiums. // J. Chem. Soc. Chem. Commun. 1996. — P. 2359−2360
765. O’Brien P. Recent advances in asymmetric synthesis using chiral lithium amide bases. // J. Chem. Soc., Perkin Trans. 1. 1998. — P. 1439−1458
766. Gibson S.E., Reddington E.G. Asymmetric functionalisation of tricarbonylchromium (O) complexes of arenes by non-racemic chiral bases. // J. Chem. Soc. Chem. Commun. 2000. — P. 989−996
767. Cowton E.L.M., Gibson S.E., Schneider M.J., Smith M.H. Chiral basemediated benzylic functionalisation of (alkyl benzyl ether) tricarbonylchromium (O) complexes. // J. Chem. Soc., Chem. Commun. 1996. — P. 839−840
768. Abecassis K., Gibson S.E., Martin-Fontecha M. Synthesis of enantioenriched secondary and tertiary alcohols via tricarbonylchromium (O) complexes of benzyl allyl ethers. // Eur. J. Org. Chem. 2009. — P. 1606−1611
769. Hoppe D., Hense T. Enantioselective synthesis with lithium/(-)-sparteine carbanion pairs. // Angew. Chem. Int. Ed. 1997. — V. 36. — P. 2282−2316
770. Price D.A., Simpkins N.S., MacLeod A.M., Watt A.P. A study of the synthesis and racemisation of a chiral lithiated tricarbonyl (^6-anisole)chromium complex. // Tetrahedron Lett. 1994. — V. 35. — P. 61 596 162
771. Koide H., Hata T., Uemura M. Asymmetric synthesis of axially chiral benzamides and anilides by enantiotopic lithiation of prochiral arene chromium complexes. // J. Org. Chem. 2002. — V. 67. — P. 1929−1935
772. Gibson S.E., Ibrahim H., Pasquier C., Steed J.W. Application of chiral lithium amide base chemistry to the synthesis of planar chiral (arene)tricarbonylchromium (O) complexes. // Tetrahedron. 2002. — V. 58. -P. 4617−4627
773. Gibson S.E., Ibrahim H. A versatile synthesis of planar chiral ligands. // Chem. Commun. 2001. — P. 1070−1071
774. Castaldi M.P., Gibson S.E., Rudd M., White A.J.P. Introduction of multiple elements of chirality around an aromatic core and an approach to enantiomerically pure C3-symmetric ligands. // Angew. Chem. Int. Ed. -2005. V. 44. — P. 3432−3435
775. Castaldi M.P., Gibson S.E., Rudd M., White A.J.P. A new approach to enantiopure C3-symmetric molecules. // Chem. Eur. J. 2006. — V. 12. — P. 138−148
776. Brewer A.R.E., Drake A.F., Gibson S.E., Rendell J.T. Interplay between core and peripheral chirality in polyethers. // Org. Lett. 2007. — V. 9. — P. 3487−3490
777. Brewer A.R.E., Drake A.F., Gibson S.E., Rendell J.T. Synthesis and CD spectroscopy of polyethers with homochiral and heterochiral layers of stereocentres. // Tetrahedron. 2008. — V. 64. — P. 6615−6627
778. Uemura M., Hayashi Y., Hayashi Y. Enantioselective ortho lithiation of tricarbonyl (masked phenol and aniline) chromium complexes. // Tetrahedron: Asymmetry. 1994. — V. 5. — P. 1427−1430
779. Gibson S.E., Ibrahim H. Asymmetric catalysis using planar chiral arene chromium complexes. // Chem. Commun. 2002. — P. 2465−2473
780. Carbone G., O’Brien P., Hilmersson G. Asymmetric deprotonation using s-BuLi or z'-PrLi and chiral diamines in THF: The diamine matters. // J. Amer. Chem. Soc.-2010. V. 132.-P. 15 445−15 450
781. Tan Y.-L., White A.J.P., Widdowson D.A., Wilhelm R., Williams D.J. Dilithiation of arenetricarbonylchromium (O) complexes with enantioselective quench: application to chiral biaryl synthesis. // J. Chem. Soc., Perkin Trans. 1. 2001. — P. 3269−3280
782. Blagg J., Davies S.G., Goodfellow C.L., Sutton K.H. The diastereoselective functionalisation of arene tricarbonylchromium complexes containing a benzylic heteroatom substituent. // J. Chem. Soc., Perkin Trans. 1. 1987. -P. 1805−1811
783. Hayashi Y., Sakai H., Kaneta N., Uemura M. New chiral chelating phosphine complexes containing tricarbonyl^-arene) chromium for highly enantioselective allylic alkylation. // J. Organomet. Chem. 1995. — V. 503.-P. 143−148
784. Uemura M., Miyake R., Shiro M., Hayashi Y. Stereoselective synthesis of (^6-arene)chromium complexes possessing chiral amine and hydroxy groups: chiral ligands in asymmetric synthesis. // Tetrahedron Lett. 1991. -V. 32.-P. 4569−4572
785. Prim D., Andrioletti В., Rose-Munch F., Rose E., Couty F. Bimetallic Pd/Cr and Pd/Mn activation of carbon-halide bonds in organochromium and organomanganese complexes. // Tetrahedron. 2004. — V. 60. — P. 3325−3347
786. Несмеянов A.H., Половянюк И. В., Макарова Л. Г. Биядерные производные карбонилов металлов с различной координацией последних с фенильным ядром молекулы // Докл. АН СССР. 1976. -Т. 230.-С. 1351−1352
787. Hunter A.D. jt? Complexes of benzene. // Organometallics. 1989. — V. 8.-P. 1118−1120
788. Jones G.B., Heaton S.B., Chapman B.J., Guzel M. On the origins of enantioselectivity in oxazaborolidine mediated carbonyl reductions. // Tetrahedron: Asymmetry. 1997. — V. 8. — P. 3625−3636
789. Kamikawa K., Uemura M. Stereoselective synthesis of axially chiral biaryls utilizing planar chiral (arene)chromium complexes. // Synlett. -2000.-P. 938−949
790. Uemura M., Nishimura H., Kamikawa K., Nakayama K., Hayashi Y. Mono-Cr (CO)3 complexes of biphenyl compounds: Cross-coupling reactions of (^6-arene)chromium complexes with arylmetals. // Tetrahedron Lett. 1994. — V. 35. — P. 1909−1912
791. Prim D., Planas J.G., Auffrant A., Rose-Munch F., Rose E., Vaissermann J. Synthesis of tricarbonyl rf- and rf-(3-thiophenyl)organo.chromium and -manganese complexes. // J. Organomet. Chem. 2003. — V. 688. — P. 273 279
792. Uemura M., Kamikawa K. Stereoselective induction of an axiel chirality by Suzuki cross coupling of tricarbonyl (arene)chromium complexes witharylboronic acids. // J. Chem. Soc., Chem. Commun. 1994. — P. 26 972 698
793. Nelson S.G., Hilfiker M.A. Asymmetric synthesis of monodentate phosphine ligands based on chiral 7/6-Crarene. templates. // Org. Lett. -1999.-V. l.-P. 1379−1382
794. Kamikawa K., Sakamoto T., Uemura M. Inversion of planar chirality vs axial isomerization of axially chiral biaryl chromium complexes. // Synlett. -2003.-P. 516−518
795. Watanabe T., Kamikawa K., Uemura M. Synthesis of both axially chiral biaryls by cross-coupling of (arene)chromium complexes with naphthylboronic acids and subsequent axial isomerization. // Tetrahedron Lett. 1995. — V. 36. — P. 6695−6698
796. Kamikawa K., Uemura M. Diastereoselective synthesis of axially chiral biaryls via nucleophilic addition to (arene)chromium complexes with Grignard reagents. // Tetrahedron Lett. 1996. — V. 37. — P. 6359−6362
797. Kundig E.P., Ratni H., Crousse B., Bernardinelli G. Intramolecular Pd-catalyzed carbocyclization, Heck reactions, and aryl-radical cyclizations with planar chiral arene tricarbonyl chromium complexes. // J. Org. Chem. -2001.-V. 66.-P. 1852−1860
798. Jackson R.F.W., Turner D., Block M.H. Direct synthesis of metal-complexed aromatic amino acid derivatives by palladium-catalysed coupling processes. // Synlett. 1996. — P. 862−864
799. Gotov B., Kaufmann J., Schumann H., Schmalz H.-G. Pd-Catalyzed cross-coupling of chloroarene-Cr (CO)3 complexes with stabilized organoindium (III) reagents under remarkably mild conditions. // Synlett. -2002.-P. 361−363
800. Mathews N., Widdowson D.A. Chromium mediated organic synthesis: The introduction of 1,1 -dimethylallyl and linalyl groups on to arenes. // Synlett. -1990.-P. 467−468
801. Weber I., Jones G.B. Bidentate planar chiral rf-arene tricarbonyl chromium (O) complexes: ligands for catalytic asymmetric alkene hydrosilylation. // Tetrahedron Lett. 2001. — V. 42. — P. 6983−6986
802. Braun W., Calmuschi-Cula B., Salzer A., Groehn V. Diastereoselective hydrogenation of folic acid esters with the Daniphos ligand. // J. Organomet. Chem. 2006. — V. 691. — P. 2263−2269
803. Gibson S.E., Ibrahim H., Pasquier C., Swamy V.M. Novel planar chiral diphosphines and their application in asymmetric hydrogenations and asymmetric Heck reactions. // Tetrahedron: Asymmetry. 2004. — V. 15. -P. 465−473
804. Gibson S.E., Rendell J.T., Rudd M. A versatile approach to planar chiral monophosphane ligands. // Synthesis. 2006. — P. 3631−3638
805. Kundig E.P., Cannas R., Laxmisha M., Ronggang L., Tchertchian S. Chromium-mediated asymmetric synthesis of both enantiomers ofacetoxytubipofuran. // J. Amer. Chem. Soc. 2003. — V. 125. — P. 56 425 643
806. Dehmel F., Schmalz H.-G. Unexpected endo selectivity of conjugate nucleophilic addition to an arene-Cr (CO)3 complex: Enantioselective synthesis of the diterpene 11 -epz'-helioporin B. // Org. Lett. 2001. — V. 3. -P. 3579−3582
807. Dehmel F., Lex J., Schmalz H.-G. An approach to serrulatane diterpenes via erafo-selective conjugate nucleophilic addition to arene-Cr (CO)3 complexes. // Org. Lett. 2002. — V. 4. — P. 3915−3918
808. Schwarz O., Brun R., Bats J.W., Schmalz H.-G. Synthesis and biological evaluation of new antimalarial isonitriles related to marine diterpenoids. // Tetrahedron Lett. 2002. — V. 43. — P. 1009−1013
809. Watanabe Т., Tanaka Y., Shoda R., Sakamoto R., Kamikawa K., Uemura M. Stereoselective synthesis of atropisomeric korupensamines A and В utilizing planar chiral arene chromium complex. // J. Org. Chem. 2004. -V. 69.-P. 4152−4158
810. Сеткина В. H., Баранецкая Н. К., Анисимов К. Н., Курсанов Д. Н. Изотопный обмен атомов водорода бензолхромтрикарбонила. // Изв. АН СССР, серия хим. 1964. — С. 1873−1874
811. Курсанов Д. Н., Сеткина В. Н., Баранецкая Н. К., Анисимов К. Н. Влияние метальной группы на скорость изотопного обмена водорода в о-, м- и и-положениях толуолхромтрикарбонила в щелочных средах. // Изв. АН СССР, серия хим. 1968. — С. 1622
812. Сеткина В. Н., Баранецкая Н. К., Анисимов К. Н., Курсанов Д. Н. Влияние заместителей в аренхромтрикарбонильных комплексах на реакцию изотопного обмена водорода в щелочной среде. // Изв. АН СССР, серия хим. 1970. — С. 473−474
813. М.В.Антонова, С. К. Моисеев, В. Н. Калинин, И. О. Шапиро. Кинетическая СН-кислотность бензолтрикарбонилхрома и его замещенных. // Изв. АН СССР, серия хим. 1989. — С. 2458−2461
814. Антонова М.В., Моисеев С. К., Калинин В. Н., Шапиро И. О. Кинетика металлирования бензолтрикарбонилхрома и его метилзамещенных. // IV Всес. конф. по металлоорг. химии, Казань, 1988. Тезисы докл. -Казань.- 1988.-Ч. 1.-С. 80
815. Антонова М.В., Моисеев С. К., Калинин В. Н., Шапиро И. О. Кинетическая кислотность СН-связей бензолтрикарбонилхрома и его метилзамещенных. // V Московская конф. по органической химии и технологии, 6−8 июня 1989 г. Тезисы докл. — М. — 1989. -Ч. 2.-С. 195
816. Шапиро И.О., Якушин Ф. С., Романский И. А., Шатенштейн А. И. Кинетический изотопный эффект в реакциях протофильного изотопного обмена водорода СН-кислот с диметилсульфоксидом. // Кинетика и катализ. 1968. — Т. 9. — С. 1011 -1015
817. Шатенштейн А.И., Романский И. А., Шапиро И. О. Различное влияние оснований на кинетическую кислотность СН-кислот. // Реакционная способность органических соединений. — 1970. Т. 7. — С. 337−355
818. J. Е. Hofmann, R. J. Muller, A. Schriesheim. Ionization Rates of Weak Acids. I. Base-Catalyzed Proton Exchange between Toluene and Tritiated Dimethyl Sulfoxide. // J. Amer. Chem. Soc., 85, {19), 3000−3002(1963)
819. Hofmann J.E., Muller R.J., Schriesheim A. Ionization rates of weak acids. II. Base-catalyzed proton exchange between polyalkylbenzenes and tritiated dimethyl sulfoxide. // J. Amer. Chem. Soc. 1963. — V. 85. -P. 3002−3006
820. Шапиро И.О., Раннева Ю. И., Шатенштейн А. И. Исследование зависимости коэффициента Бренстеда от протофильности катализатора в реакциях ионизации ароматических связей СН бензола и его производных. // Журн. общей химии. 1979. — Т. 49. -С. 2030−2036
821. Калинин В.Н., Удалов Н. И., Усатов A.B. Синтез арилпропионовых кислот через^{-металлирование} (алкиларен)хромтрикарбонилов. // Изв. АН СССР, серия хим. 1987. — С. 1672−1673
822. Калинин В.Н., Моисеев С. К., Бахмутов В. И., Удалов Н. И. Синтез 6,7-бензоморфанов с использованием аренхромтрикарбонильных комплексов. // Rev. Roumaine Chim. 1989. — V. 34. — P. 503−508
823. Kalinin V.N., Moiseev S.K., Bakhmutov V.l., Cherepanov I.A. Arenetricarbonylchromium complexes in the synthesis of 6,7-benzomorphanes. // J. Organometal. Chem. 1990. — V. 383. — P. 85−91
824. Muller Т.Е., Beller M. Metal-initiated amination of alkenes and alkynes. // Chem. Rev. 1998. — V. 98. — P. 675−704
825. Molander G.A., Romero J.A.C. Lanthanocene catalysts in selective organic synthesis. // Chem. Rev. 2002. — V. 102. — P. 2161−2186
826. Schlummer B., Hartwig J.F. Bronsted acid-catalyzed intramolecular hydroamination of protected alkenylamines. Synthesis of pyrrolidines and piperidines. // Org. Lett. 2002. — V. 4. — P. 1471−1474
827. Beller M., Breindl C., Riermeier T.H., Eichberger M., Trauthwein H. Base-catalyzed synthesis of Ar-(2-arylethyl)anilines and base-promoted domino synthesis of 2,3-dihydroindoles. // Angew. Chem., Int. Ed. -1998.-V. 37.-P. 3389−3391
828. Beller M., Breindl C. Base-catalyzed hydroamination of aromatic olefins an efficient route to l-aryl-4-(arylethyl)piperazines. // Tetrahedron. — 1998. — V. 54. — P. 6359−6368
829. Seijas J.A., Vazquez-Tato M.P., Entenza C., Martinez M.M., Onega M.G., Veiga S. Synthesis of /?-phenylethylamines from styrene derivatives. // Tetrahedron Lett. 1998. — V. 39. — P. 5073−5076
830. Kawatsura M., Hartwig J.F. Palladium-catalyzed intermolecular hydroamination of vinylarenes using arylamines. // J. Amer. Chem. Soc. 2000. — V. 122. — P. 9546−9547
831. Molander G.A., Dowdy E.D. Lanthanide-catalyzed hydroamination of hindered alkenes in synthesis: Rapid access to 10,11-dihydro-5//-dibenzo- a,?/.cyclohepten-5,10-imines. // J. Org. Chem. 1999. — V. 64.-P. 6515−6517
832. Molander G.A., Dowdy E.D., Pack S.K. A diastereoselective intramolecular hydroamination approach to the syntheses of (+)-, (±)-, and (-)-pinidinol. // J. Org. Chem. 2001. — V. 66. — P. 4344−4347
833. Ryu J.-S., Marks T.J., McDonald F.E. Organolanthanide-catalyzed intramolecular hydroamination/cyclization of amines tethered to 1,2-disubstituted alkenes. // Org. Lett. 2001. — V. 3. — P. 3091−3094
834. Cheng C., Sun J., Xing L., Xu J., Wang X., Hu Y. Highly chemoselective Pd-C catalytic hydrodechlorination leading to the highly efficient N-debenzylation of benzylamines. // J. Org. Chem. 2009. — V. 74.-P. 5671−5674
835. Wang X., Dong Y., Sun J., Xu X., Li R., Hu Y. Nonracemic Betti base as a new chiral auxiliary: Application to total syntheses of enantiopure (2S, 6R)~ dihydropinidine and (25', 6i?)-isosolenopsins. // J. Org. Chem. 2005. — V. 70.-P. 1897−1900
836. Калинин В.Н., Черепанов И. А., Моисеев С. К. Селективное металлирование алкиларенхромтрикарбонилов в бензильное положение амидами лития. // Металлоорганич. химия. 1991. — Т. 4.-С. 177−181
837. Kalinin V.N., Cherepanov I.A., Moiseev S.K. Benzylic functionalization of (^6-alkylarene) chromiumtricarbonyl complexes. // J. Organometal. Chem. 1997. — V. 536−537. — P. 437−455
838. McGrew G.I., Temaismithi J., Carroll P.J., Walsh P.J. Synthesis of polyarylated methanes through cross-coupling of tricarbonylchromium-activated benzyllithiums. // Angew. Chem. Int. Ed. (Engl.). 2010. — V. 49.-P. 5541−5544
839. Zhang J., Stanciu C., Wang В., Hussain M.M., Da C.-S., Carroll P.J., Dreher S.D., Walsh P.J. Palladium-catalyzed allylic substitution with (^6-arene-CH2Z)Cr (CO)3-based nucleophiles. // J. Amer. Chem. Soc. -2011. V. 133. — P. 20 552−20 560
840. Trost B.M., van Vranken D.L. Asymmetric transition metal-catalyzed allylic alkylations. // Chem. Rev. 1996. — V. 96. — P. 395−422
841. Trost B.M., Crawley M.L. Asymmetric transition-metal-catalyzed allylic alkylations: applications in total synthesis. // Chem. Rev. 2003. -V. 103.-P. 2921−2943
842. Blagg J., Davies S.G. Stereospecific conversion of N, N-dimethylamphetamine into iV-methylpseudoephedrine. // J. Chem. Soc., Chem. Commun. 1985. — P. 653−654
843. Моисеев C.K., Черепанов И. А., Калинин B.H. Использование (алкиларен)хромтрикарбонилов в синтезе «-фенилкарбоновыхкислот. // V Всес. конф. по металлоорг. химии, Юрмала, 1 -4 апреля 1991 г. Тезисы докл. — Рига. — 1991. — С. 210
844. Калинин В.Н., Черепанов И. А., Моисеев С. К. (if-Арен)хромтрикарбонильные комплексы в органическом синтезе. Синтез 2-арилкарбоновых кислот и С-норбензоморфанов. // Металлоорганич. химия. 1992. Т. 5. — С. 1356−1363
845. Kalinin V.N., Cherepanov I.A., Moiseev S.K. Synthesis of 2-arylcarboxylic acids and C-norbenzomorphans via if-arenetricarbonylchromium complexes. // Mendeleev Commun. 1992. -P. 113−114
846. Shen T.Y. Perspectives in nonsteroidal anti-inflammatory agents. // Angew. Chem. Int. Ed. 1972. — V. 11. — P. 460−472
847. Rieu J.-P., Boucherie A., Cousse H., Mouzin G. Methods for the synthesis of antiinflammatory 2-aryl propionic acids. // Tetrahedron. -1986.-V. 42.-P. 4095−4131
848. Kalinin V.N., Cherepanov I.A., Moiseev S.K. 1,2- and 1,4-addition reactions of
849. Шульпин Г. Б. // Органические реакции, катализируемые комплексами металлов. М. — Наука. — 1988. — С. 247
850. Kalinin V.N., Cherepanov I.A., Moiseev S.K. Benzylic organozinc derivatives of (^6-alkylarene)tricarbonylchromium complexes: cross-coupling reactions with organic halides. // Mendeleev Commun. 1994. -P. 53−55
851. O’Brien P. Cadmium and zinc // In: Comprehensive Organometallic Chemistry II. Abel E.W., Gordon F., Stone A., Wilkinson G. (Eds.). -Pergamon. — 1995. -V. 3.-P. 175−206
852. Бацанов A.C., Стручков Ю. Т. И Проблемы кристаллохимии. — M. — Наука. 1987.-С. 7
853. Rees В., Coppens P. Electronic structure of benzene chromium tricarbonyl by X-ray and neutron diffraction at 78 K. // Acta Crystal. 1973. — V. B29. -P. 2516−2528
854. Kalinin V.N., Cherepanov I.A., Moiseev S.K., Dolgushin F.M., Yanovsky A.I., Struchkov Yu.T. 2-^-AUyl-l, l, l-tricarbonyl-//-(/7-: rf. diphenylmethyl) chromi-umpalladium (Pd-Cr) at 13 OK. // Acta Cryst. -1993.-V. C49. P. 805−808
855. Watts W.E. Ferrocenylcarbocations and related species. // J. Organometal. Chem. Libr. 1979. — V. 7. — P. 399−459
856. Калинин В.Н., Баханова И. В., Кобак В. В., Моисеев С. К. Этиленкеталь 14/?-гидрокси-17-нор-17-фенилдигидрокодеинона -первое iV-арильное производное морфиновых алкалоидов. // Изв. АН. Сер. хим. 1997. — С. 879−880
857. Abramovitch R.A., Burton D.H.R., Finet J.P. Newer methods of arylation. // Tetrahedron. 1988. — V. 44. — P. 3039−3071
858. Arnauld Т., Burton D.H.R., Doris E. The chemistry of pentavalent organobismuth reagents. Part 14. Recent advances in the copper-catalyzed phenylation of amines. // Tetrahedron. 1997. — V. 53. — P. 4137−4144
859. Suzuki H., Matano Y. Organobismuth compounds: synthesis, properties and uses in organic transformations. // In: Chemistry of arsenic, antimony, and bismuth. Norman N.C. (Ed.). — Blackie Academic and Professional. — London. — 1998. — P. 283−344
860. Моисеев C.K., Баханова И. В., Шмидхаммер Г., Калинин В. Н. Синтез jV-фенилзамещенных производных морфиновых алкалоидов. // Изв. АН. Сер. хим. 1999. — С. 595−598