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 journalArticle

32 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)4972-4975
Number of pages4
JournalAngewandte Chemie - International Edition
Volume51
Issue number20
DOIs
Publication statusPublished - May 14 2012
Externally publishedYes

Keywords

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

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

Fingerprint Dive into the research topics of 'Total synthesis of (-)-13-oxyingenol and its natural derivative'. Together they form a unique fingerprint.

  • Cite this

    Ohyoshi, T., Funakubo, S., Miyazawa, Y., Niida, K., Hayakawa, I., & Kigoshi, H. (2012). Total synthesis of (-)-13-oxyingenol and its natural derivative. Angewandte Chemie - International Edition, 51(20), 4972-4975. https://doi.org/10.1002/anie.201201383