Gold(I)-Catalyzed Tandem Transformation with Diynes: Rapid Access to Linear Cyclopentenone-Fused Polycyclic Molecules.

Abstract

An efficient and convenient synthesis of useful linear cyclopentenone-fused polycyclic compounds has been achieved through a novel gold(I)-catalyzed transformation of diynes. The method demonstrates high product yields and tolerates of a wide variety of important functional groups. Gold-vinylidene formation, methoxy group migration, and Nazarov-type cyclization are proposed to be the key steps in the reaction pathway. The synthetic utility of this method is demonstrated by converting the product to eight-membered-ring-fused compound.