An Efficient Method for the Optical Resolution of 3-Hydroxy-2-substituted-4-alkynoates: A Highly Stereoselective Total Synthesis of (+)-Bengamide E

Article abstract of DOI:10.1021/jo00123a030

A novel procedure for the optical resolution of 3-hydroxy-2-substituted-4-alkynoates and its application to the stereoselective total synthesis of (+)-bengamide E are described. 3-Hydroxy-2-substituted-4-alkynoates, derived from the aldol reaction of cobalt-complexed propynals with ketene O-silyl O,S-acetals, were easily resolved by the formation of a chiral carbamate followed by cobalt complexation.Chiral 2-(benzyloxy)-3-hydroxy-4-alkynoate derivatives thus obtained were used as starting materials for a highly stereoselective total synthesis of (+)-bengamide E.