Enantioselective Synthesis of the Guaipyridine Alkaloid (+)- and (-)-Cananodine.

ABSTRACT: Synthesis of both enantiomers of guaipyridine alkaloid cananodine was achieved. The stereocenter at C8 was set through an Evans alkylation, and the seven-membered carbocycle was constructed using an intramolecular Mizoroki-Heck reaction. Hydrogenation of an exomethylene set the C5 stereocenter. The optical rotation of each enantiomer matched the literature. The synthetic scheme is amenable to analogue preparation. (+)- and (-)-Rupestine G were also prepared.

SUBMITTER: Holliday HM 

PROVIDER: S-EPMC10882590 | biostudies-literature | 2024 Feb

REPOSITORIES: biostudies-literature