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

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

doi:10.1021/ol026338a

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

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

Department of Applied Chemistry

Research output: Contribution to journal › Article › peer-review

53 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 language	English
Pages (from-to)	2941-2943
Number of pages	3
Journal	Organic Letters
Volume	4
Issue number	17
DOIs	https://doi.org/10.1021/ol026338a
Publication status	Published - 2002 Aug 22

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol026338a

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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.",

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AU - Yasui, Hiroyuki

AU - Tadano, Kin Ichi

PY - 2002/8/22

Y1 - 2002/8/22

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

Abstract

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