Enantioselective Synthesisof (+)-l-733,060 and (+)-CP-99,994:Application of an Ireland-Claisen Rearrangement/MichaelAddition Domino Sequence

An efficient asymmetric synthesis of (+)-L-733,060, (―)-(2S,3R)-1 and (+)-CP-99,994, starting from a Baylis―Hillman adduct, is described. The key steps include a novel domino reaction: stereoselective Ireland―Claisen rearrangement, asymmetric Michael addition, and piperidone ring formation through a one-pot reaction hydrogenolysis/lactamization and a stereoselective inversion of a hydroxy group.