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 ...