A gram-scale route to phlegmarine alkaloids: rapid total synthesis of (−)-cermizine B

Abstract

The synthesis of the Lycopodium alkaloid (−)-cermizine B (1), which establishes its absolute configuration, is achieved by combining asymmetric organocatalysis and an uninterrupted eight-step reaction sequence, followed by a final reduction step. This “pot-economy” strategy provides access to the cis-phlegmarine stereoparent embedded in 1 for the first time, rapidly and on a gram-scale.