Concise Synthesis of (-)-isoaltholactone and (±)-5-epi-OBn-Goniotriol

Abstract

Concise route for the synthesis of (-)-isoaltholactone and (±)-5-epi-OBn-Goniotriol were described. Key features for the (-)-isoaltholactone synthesis involved; a) diastereoselective and enantioselective aldol reaction between chiral pyrrolidine substituted γ-benzyloxy vinylogous urethane enolate and cinnamaldehyde afforded highly stereoselective syn δ-lactone, b) allylic 1,3-strain controlled epoxidation of styryl alkene following the stereospecific opening of the epoxide assisted by a proximal benzyloxy group completed the synthesis. Reaction of simple pyrrolidine substituted γ-benzyloxy vinylogous urethane enolate and cinnamaldehyde gave anti δ-lactone. Epoxidation and epoxide opening of the styryl alkene substrate of anti δ-lactone derivative was also investigated, which led to the synthesis of (±)-5-epi-OBn-Goniotriol.