Enantioselective Total Synthesis of (+)-Cylindricine B

Abstract

This article describes the first enantioselective synthesis of the Tasmanian marine alkaloid (+)-cylindricine B. The concise construction of the compound hinged on dearomative retrosynthetic logic combined with a tactical advance in the generation of congested, cyclic, alpha-tertiary amine centers. The scope of this key coupling reaction was explored in addition to providing a synthetic application for Cu-catalyzed enantioselective dearomatization of N-acyl-pyridiniums. The synthesis proceeds in five or six steps from commercially available starting materials.