Total Synthesis of (−)-Dihydrosporothriolide Utilizing an Indium-Mediated Reformatsky–Claisen Rearrangement

Abstract

The asymmetric synthesis of (−)-dihydrosporothriolide (<b>1</b>), a biologically active bis-γ-butyrolactone, is described, that proceeds through a d-proline-catalyzed asymmetric aminooxylation, indium-mediated Reformatsky–Claisen rearrangement of an α,α-dibromoacetate derivative, and diastereoselective dihydroxylation. The route requires no protective group manipulation and allows the concise seven-step synthesis of <b>1</b> from <i>n</i>-octanal