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Keywords:

  • 13-oxyingenol;
  • inside–outside framework;
  • metathesis;
  • sigmatropic rearrangement;
  • terpenoids
Thumbnail image of graphical abstract

Ring functionalization: The total synthesis of a natural derivative of (−)-13-oxyingenol, a potent anti-HIV diterpenoid, is reported. The key steps in this synthesis include a ring-closing olefin metathesis and a Mislow–Evans-type [2,3]-sigmatropic rearrangement. This synthesis provides access to (−)-13-oxyingenol and its natural derivative in 21 steps from a synthetic intermediate previously prepared by Kigoshi and co-workers.