Lewis-Acid-Catalyzed Activation of Zerumbone towards Sesquiterpenoid Derivatives: Sustainable Utilization of Abundant Natural Resources for the Synthesis of Chemically Diverse Architectures

Abstract

A facile Lewis-acid-catalyzed method for the synthesis of structurally diverse sesquiterpenoid derivatives from readily available and abundant 11-membered natural product zerumbone has been developed. Starting from zerumbone, we have developed an efficient cyclization process for the creation of [5.7], [5.8], and [5.8.3] fused-ring systems. This process was exemplified by the selective functionalization of zerumbone; by controlling the conformation of the 11-membered ring, the ring-closing process could be tuned to afford the fused-ring system of choice.