The isomeric 3-Oxa-and 3-thiagranatanin-7-ols and their derivatives; reduction of bicyclic amino ketones related to tropinone1, 2

CL ZIRKLE, FR GERNS, AM PAVLOFF…

Index: Zirkle,C.L. et al. Journal of Organic Chemistry, 1961 , vol. 26, p. 395 - 407

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Citation Number: 33

Abstract

A pseudopelletierine analog, 9-methyl-3-oxsgranatanin-7-one (III), was prepared by the Robinson-Sch6pf condensation of oxydiacetaldehyde, methylamine, and acetonedicarboxylic acid. Reduction of this ketone and ita 3-this analog (V) by various methods gave epimeric 9-methyl-3-oxa-and 9-methyl-3-thiagranatanin-7-and 7Mls (IVA-IVB; VIA-VIB). In contrast to the related ketones tropinone (IX) and" homopseudopelletierine"(XI ...