Total synthesis of (±)-mycoepoxydiene, a novel fungal metabolite having an oxygen-bridged cyclooctadiene skeleton

Ken Ichi Takao, Gohshi Watanabe, Hiroyuki Yasui, Kin Ichi Tadano

Research output: Contribution to journalArticle

49 Citations (Scopus)

Abstract

The first total synthesis of (±)-mycoepoxydiene has been accomplished. A ring-closing olefin metathesis (RCM) approach was employed for the construction of the oxygen-bridged eight-membered bicyclic skeleton. The RCM product was converted to the target natural product featuring the oxidative rearrangement of a furfuryl alcohol introduced as the side chain and the stereoselective 1,2-reduction of a δ-keto-β,γ-unsaturated α-lactol intermediate.

Original languageEnglish
Pages (from-to)2941-2943
Number of pages3
JournalOrganic Letters
Volume4
Issue number17
DOIs
Publication statusPublished - 2002 Aug 22

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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