Enantioselective Desymmetrization of meso-Decalin Diallylic Alcohols by a New Zr-Based Sharpless AE Process: A Novel Approach to the Asymmetric Synthesis of Polyhydroxylated Celastraceae Sesquiterpene Cores

Abstract

Zirconium to the rescue! Eight contiguous chiral centers can be established with >95 % ee in the key step of an asymmetric synthetic approach to the cores of certain Celastraceae sesquiterpenes (see scheme). The route required the development of a new zirconium-modified Sharpless asymmetric epoxidation instead of the traditional titanium version. DIPT=diisopropyl tartrate.