Pd-Catalyzed Nazarov-Type Cyclization: Application in the Total Synthesis of β-Diasarone and Other Complex Cyclopentanoids

Abstract

We describe the palladium-catalyzed Nazarov-type cyclization of easily accessible (hetero)arylallyl acetates to pentannulated (hetero)arenes. This method provides ready access to various types of bi-, tri-, tetra-, and pentacyclic cyclopentanoids under neutral conditions. The synthetic utility is further demonstrated in the first total synthesis of βdiasarone and several other complex cyclopentanoids relevant to medicinal chemistry and materials science.