Synthesis of (3R,5S)-5-hydroxy-de-O-methyllasiodiplodin: a facile and stereoselective approach

Abstract

A concise and facile synthesis of (3R,5S)-5-hydroxy-de-O-methyllasiodiplodin has been demonstrated in 12steps starting from methylacetoacetate and (±)propylene oxide. The key reactions involved are Jacobsen’s hydrolytic kinetic resolution, Sharpless asymmetric epoxidation, Mitsunobu, and ring closing metathesis reaction for the construction of macrolactone with two chiral substitutions on it.