Stereoselective Total Synthesis of Proposed Structure of Stagonolide D

Abstract

The stereoselective total synthesis of the proposed structure of naturally occurring nonenolide stagonolide D has been achieved using D-mannitol as the starting material. The latter has been utilized for the preparation of both the olefinic alcohol segment and the olefinic acid segment of the target molecule. The synthetic sequence involves asymmetric epoxidation and ring-closing metathesis as the key steps.