Stereoselective total synthesis of clonostachydiol

Abstract

A simple and efficient stereoselective synthesis of clonostachydiol was achieved using ethyl (R)-3-hydroxybutanoate 5 and methyl (R)-2-hydroxypropanoate 12 as readily available starting materials. The key steps involved in the synthesis were MacMillan α-hydroxylation, Horner–Wadsworth–Emmons (HWE) olefination, a Grignard reaction, and Hoveyda–Grubbs IInd generation catalyzed ring closing metathesis (RCM).