Total synthesis of (-)-13-oxyingenol and its natural derivative

Takayuki Ohyoshi, Shota Funakubo, Yamato Miyazawa, Keisuke Niida, Ichiro Hayakawa, Hideo Kigoshi

Research output: Contribution to journalArticlepeer-review

38 Citations (Scopus)


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.

Original languageEnglish
Pages (from-to)4972-4975
Number of pages4
JournalAngewandte Chemie - International Edition
Issue number20
Publication statusPublished - May 14 2012


  • 13-oxyingenol
  • inside-outside framework
  • metathesis
  • sigmatropic rearrangement
  • terpenoids

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)


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