Stereoselective Total Synthesis of (-)-Ebelactone A

A highly stereoselective total synthesis of the beta-lactam inhibitor of several therapeutically important enzymes, (-)-ebelactone A (1) is described. The salient features of this synthesis include desymmetrization of bicyclic symmetric olefin with Brown's asymmetric hydroboration, Wittig olefination, Evans ' alkylation, Sharpless asymmetric epoxidation, Gillman's reaction, TEMPO-BAIB mediated selective oxidation of 1,3-diol and Adam's beta-lactonization.