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Keywords:

  • asymmetric synthesis;
  • bioinspired synthesis;
  • radical coupling;
  • total synthesis

Abstract

The first asymmetric total synthesis of (−)-ophiodilactone A and (−)-ophiodilactone B, isolated from the ophiuroid (Ophiocoma scolopendrina), is reported. The key features of the synthesis include the highly stereocontrolled construction of the structurally congested γ-lactone/δ-lactone skeleton through an asymmetric epoxidation, diastereoselective iodolactonization, and intramolecular epoxide-opening with a carboxylic acid, and biomimetic radical cyclization of ophiodilactone A to ophiodilactone B.