Abstract
A method for the preparation ofN-phenyl-substituted morphine alkaloids by treatment of the correspondingN-nor derivatives with Ph3Bi in the presence of Cu(OAc)2 is proposed. 17-Nor-17-phenylthebaine thus obtained can serve as a convenient starting material for the preparation of otherN-phenyl-substituted alkaloids.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
G. R. Lenz, S. M. Evans, D. E. Walters and A. J. Hopfinger, inOpiates, publs. Harcourt, Brace, Jovanovich, Acad. Press, Inc., Orlando-London, 1986, a) p. 72; b) p. 102.
V. N. Kalinin, I. V. Bakhanova, V. V. Kobak, and S. K. Moiseev,Izv. Akad. Nauk, Ser. Khim., 1997, 879 [Russ. Chem. Bull., 1997,46, 845 (Engl. Transl.)].
R. A. Abramovitch, D. H. R. Burton, and J. P. Finet,Tetrahedron, 1988,44, 3039; T. Arnauld, D. H. R. Burton, and E. Doris,Tetrahedron, 1997,53, 4137 and references therein.
Neth. Appl. 6515815;Chem Abstr., 1966,65, 15441d.
Brit. Pat. 1136214;Chem. Abstr., 1966,70, 78218s.
F. M. Hauser, Tek-Kuei Chen, and F. I. Carroll,J. Med. Chem., 1974,17, 1117.
K. W. Bentley and D. G. Hardy,J. Am. Chem. Soc., 1967,89, 3267.
I. V. Bakhanova, V. N. Nesterov, S. K. Moiseev, H. Shmidhammer, and V. N. Kalinin,Izv. Akad. Nauk, Ser. Khim., 1998, 2245 [Russ. Chem. Bull., 1998,47, 2177 (Engl. Transl.)].
Author information
Authors and Affiliations
Additional information
Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 595–598, March, 1999.
Rights and permissions
About this article
Cite this article
Moiseev, S.K., Bakhanova, I.V., Schmidhammer, H. et al. Synthesis ofN-phenyl-substituted derivatives of morphine alkaloids. Russ Chem Bull 48, 589–592 (1999). https://doi.org/10.1007/BF02496186
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF02496186