Enantioselective Total Synthesis of (-)-Zampanolide, a Potent Microtubule-Stabilizing Agent

An enantioselective total synthesis of zampanolide has been accomplished using a novel DDQ/Bronsted acid promoted cyclization as the key reaction. The synthesis features cross-metathesis to construct the trisubstituted olefin and a ring-closing metathesis to form the macrolactone. The final N-acyl aminal formation was stereoselectively accomplished by an organocatalytic reaction.