Enantioselective total synthesis of ()-nakinadine B

A novel approach for the synthesis of α-phenyl-β 2 -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. A novel approach for the synthesis of ( S )-nakinadine B, a marine natural product is described. The synthesis utilizes the optimized combination of organocatalyzed Michael addition and aminoxylation reactions as key steps.