A simple and efficient stereoselective synthesis of (−)-cleistenolide

Abstract

A simple and straightforward stereoselective synthesis of α,β-unsaturated δ-lactone, (−)-cleistenolide has been accomplished in 10 steps in an overall yield of 19%, starting from inexpensive and commercially available starting materials, respectively. This linear synthesis utilizes Sharpless asymmetric dihydroxylation, sulfur ylide mediated epoxide opening followed by ring-closing metathesis (RCM) for the formation of six-membered lactone ring as the key step sequence.