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

28 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

Fingerprint

Derivatives
Diterpenes
Alkenes
Olefins
13-oxyingenol

Keywords

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

ASJC Scopus subject areas

  • Chemistry(all)
  • Catalysis

Cite this

Total synthesis of (-)-13-oxyingenol and its natural derivative. / Ohyoshi, Takayuki; Funakubo, Shota; Miyazawa, Yamato; Niida, Keisuke; Hayakawa, Ichiro; Kigoshi, Hideo.

In: Angewandte Chemie - International Edition, Vol. 51, No. 20, 14.05.2012, p. 4972-4975.

Research output: Contribution to journalArticle

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, vol. 51, no. 20, pp. 4972-4975. https://doi.org/10.1002/anie.201201383
Ohyoshi, Takayuki ; Funakubo, Shota ; Miyazawa, Yamato ; Niida, Keisuke ; Hayakawa, Ichiro ; Kigoshi, Hideo. / Total synthesis of (-)-13-oxyingenol and its natural derivative. In: Angewandte Chemie - International Edition. 2012 ; Vol. 51, No. 20. pp. 4972-4975.
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