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 β-diasarone and several other complex cyclopentanoids relevant to medicinal chemistry and materials science.