A concise and stereoselective synthesis of both enantiomers of altholactone and isoaltholactone

Abstract

A concise and flexible stereoselective route to synthesize both enantiomers of the highly functionalized α,β-unsaturated-δ-lactones, altholactone and isoaltholactone, from readily available cinnamyl alcohol is described. This approach derived its asymmetry from Sharpless catalytic asymmetric epoxidation and Sharpless asymmetric dihydroxylation reactions. The resulting diols were produced in high enantiomeric excess and were cyclized in a stereoselective manner in the presence of a catalytic amount of camphor sulphonic acid. The synthesis of both enantiomers of altholactone and isoaltholactone has been achieved in a concise and highly enantioselective manner.