Synthesis of guaipyridine alkaloids (±)-cananodine and (±)-rupestines D and G using an intramolecular Mizoroki-Heck reaction

Abstract

The guaipyridine alkaloids cananodine, rupestine D and rupestine G were synthesized in six steps or less from readily available 3-(allyloxy)-2-(bromomethyl)-6-methylpyridine. Key steps in the synthesis include an enolate alkylation of the aforementioned substituted picolyl bromide and an intramolecular Mizoroki-Heck reaction to form the seven-membered carbocycle of the target compounds.