SEARCH

SEARCH BY CITATION

Keywords:

  • Natural products;
  • Total synthesis;
  • Diastereoselectivity;
  • Macrocycles;
  • Chemoselectivity;
  • Oxidation;
  • Enzyme catalysis

Abstract

A highly stereoselective first total synthesis of amphidinin B is described. The key steps involved in this synthesis are the generation of the exo-double bond in the C1–C9 segment, the Barbier allylation, enzymatic kinetic resolution, and the construction of the C10–C21 segment by Sharpless asymmetric epoxidation, base-induced epoxide ring-opening, radical cyclization, diastereoselective reduction of the exo-cyclic double bond, one-pot allylation followed by debenzylation, Evans alkylation, and Yamaguchi esterification.