Enantioselective total synthesis of (S)-nakinadine B

Abstract

A novel approach for the synthesis of α-phenyl-β²-amino acid core unit 1 and its application to the total synthesis of (S)-nakinadine B 3, a marine natural product, is described. The synthesis utilizes the optimized combination of diphenylprolinol silyl ether mediated asymmetric Michael addition and a proline catalyzed aminoxylation reactions as key steps.