Total syntheses of (±)-penicibilaenes A and B via intramolecular aldol condensation

Abstract

In this study, concise total syntheses of Peniclillium sesquiterpenes (±)-Penicibilaenes A and B are described. This approach involves an effective intramolecular aldol condensation to construct a bicyclic skeleton, a stereoselective rhodium-catalyzed 1,4-addition, a ring-closing metathesis, and several effective transformations that lead to (±)-penicibilaenes A and B with longest linear sequences of 12 and 13 steps, respectively. These transformations utilize commercial materials and are achieved in 4.0% overall yields for both compounds.