Journal of the Chemical Society. Perkin transactions I p. 1139 - 1142 (1991)
Update date:2022-08-03
Topics:
Berenyi, Sandor
Gulyas, Gyoengyi
Batta, Gyula
Gunda, Tamas
Makleit, Sandor
Azidolysis of C-19 diastereoisomer tosylesters of morphine derivatives possessing a bridged ring C has been studied and 4-azatetracyclo<4.4.02,4.03,8>decanes 6b, 6d, and 6f were formed via the substitution and subsequent intramolecular cyclization of the (R)-C-19 tosylesters 4b, 4d, and 4f, and primarily the ethylidene derivatives 7a, 7b and 7c were obtained from (S)-C-19 tosylesters 4c, 4e and 4g.According to our experience the course of the reaction depends on the configuration of the C-19 centre of chirality and on the spatial requirement of the substituent on C-6.
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