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Keywords:

  • Total synthesis;
  • Natural products;
  • Asymmetric synthesis;
  • Rearrangement;
  • Epimerization

Abstract

The first total synthesis of (+)-murolic acid is accomplished in 17 steps from ester 9 in 14.8 % overall yield. The key steps involve asymmetric dihydroxylation, orthoester Johnson–Claisen rearrangement and α-methylenation using Stiles reagent. A beneficial late stage β-epimerization reverted a stereodivergent relay to a stereoconvergent completion of an efficient synthesis of (+)-murolic acid.