A convergent total synthesis of epolactaene: An application of the bridgehead oxiranyl anion strategy

Kouji Kuramochi; Seigo Nagata; Hideyoshi Itaya; Yasuaki Matsubara; Takashi Sunoki; Hiromi Uchiro; Ken Ichi Takao; Susumu Kobayashi

doi:10.1016/j.tet.2003.09.021

A convergent total synthesis of epolactaene: An application of the bridgehead oxiranyl anion strategy

Kouji Kuramochi, Seigo Nagata, Hideyoshi Itaya, Yasuaki Matsubara, Takashi Sunoki, Hiromi Uchiro, Ken Ichi Takao, Susumu Kobayashi

Department of Applied Chemistry

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

41 Citations (Scopus)

Abstract

The generation and reaction of a lactone-derived oxiranyl anion is described. The aldol-type reaction of the epoxylactone and aldehydes was accomplished by a two-step procedure via the trimethylsilyl epoxylactone. The application of this methodology to the total synthesis of (+)-epolactaene and its analogs is described.

Original language	English
Pages (from-to)	9743-9758
Number of pages	16
Journal	Tetrahedron
Volume	59
Issue number	49
DOIs	https://doi.org/10.1016/j.tet.2003.09.021
Publication status	Published - 2003 Dec 1

Keywords

Aldol reaction
Epolactaene
Epoxylactone
TBAF

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2003.09.021

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abstract = "The generation and reaction of a lactone-derived oxiranyl anion is described. The aldol-type reaction of the epoxylactone and aldehydes was accomplished by a two-step procedure via the trimethylsilyl epoxylactone. The application of this methodology to the total synthesis of (+)-epolactaene and its analogs is described.",

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author = "Kouji Kuramochi and Seigo Nagata and Hideyoshi Itaya and Yasuaki Matsubara and Takashi Sunoki and Hiromi Uchiro and Takao, {Ken Ichi} and Susumu Kobayashi",

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T1 - A convergent total synthesis of epolactaene

T2 - An application of the bridgehead oxiranyl anion strategy

AU - Kuramochi, Kouji

AU - Nagata, Seigo

AU - Itaya, Hideyoshi

AU - Matsubara, Yasuaki

AU - Sunoki, Takashi

AU - Uchiro, Hiromi

AU - Takao, Ken Ichi

AU - Kobayashi, Susumu

PY - 2003/12/1

Y1 - 2003/12/1

N2 - The generation and reaction of a lactone-derived oxiranyl anion is described. The aldol-type reaction of the epoxylactone and aldehydes was accomplished by a two-step procedure via the trimethylsilyl epoxylactone. The application of this methodology to the total synthesis of (+)-epolactaene and its analogs is described.

AB - The generation and reaction of a lactone-derived oxiranyl anion is described. The aldol-type reaction of the epoxylactone and aldehydes was accomplished by a two-step procedure via the trimethylsilyl epoxylactone. The application of this methodology to the total synthesis of (+)-epolactaene and its analogs is described.

KW - Aldol reaction

KW - Epolactaene

KW - Epoxylactone

KW - TBAF

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U2 - 10.1016/j.tet.2003.09.021

DO - 10.1016/j.tet.2003.09.021

M3 - Article

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SN - 0040-4020

VL - 59

SP - 9743

EP - 9758

JO - Tetrahedron

JF - Tetrahedron

IS - 49

ER -

A convergent total synthesis of epolactaene: An application of the bridgehead oxiranyl anion strategy

Abstract

Keywords

ASJC Scopus subject areas

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