Total syntheses of lycoposerramine-V and 5-epi-lycoposerramine-V

Abstract

Enantioselective total syntheses of lycopodium alkaloids lycoposerramine-V and 5-epi-lycoposerramine-V have been accomplished. Features of the newly established total synthesis include: 1) introduction of the first chiral center with a scalable desymmetrization reaction of an meso-anhydride; 2) chemoselective functionalization of a bis-Weinreb-amide with Grignard addition; and 3) construction of the multifunctionalized cyclohexanone with a stereoselective intramolecular Michael addition.