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

Kenichi 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

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metabolites
metathesis
Alkenes
closing
Metabolites
musculoskeletal system
Skeleton
alkenes
furfuryl alcohol
Oxygen
rings
oxygen
synthesis
products
Biological Products
mycoepoxydiene

ASJC Scopus subject areas

  • Molecular Medicine

Cite this

Total synthesis of (±)-mycoepoxydiene, a novel fungal metabolite having an oxygen-bridged cyclooctadiene skeleton. / Takao, Kenichi; Watanabe, Gohshi; Yasui, Hiroyuki; Tadano, Kin Ichi.

In: Organic Letters, Vol. 4, No. 17, 22.08.2002, p. 2941-2943.

Research output: Contribution to journalArticle

Takao, Kenichi ; Watanabe, Gohshi ; Yasui, Hiroyuki ; Tadano, Kin Ichi. / Total synthesis of (±)-mycoepoxydiene, a novel fungal metabolite having an oxygen-bridged cyclooctadiene skeleton. In: Organic Letters. 2002 ; Vol. 4, No. 17. pp. 2941-2943.
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