A practical total synthesis of both enantiomers of epoxyquinols A and B

Mitsuru Shoji; Satoshi Kishida; Mitsuhiro Takeda; Hideaki Kakeya; Hiroyuki Osada; Yujiro Hayashi

doi:10.1016/S0040-4039(02)02271-2

A practical total synthesis of both enantiomers of epoxyquinols A and B

Mitsuru Shoji, Satoshi Kishida, Mitsuhiro Takeda, Hideaki Kakeya, Hiroyuki Osada, Yujiro Hayashi

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

37 Citations (Scopus)

Abstract

A practical total synthesis of both enantiomers of epoxyquinols A and B has been developed. Key reactions are the chromatography-free preparation of an iodolactone by using acryloyl chloride as dienophile in the Diels-Alder reaction of furan, the lipase-mediated kinetic resolution of a cyclohexenol derivative, and a modified procedure for α-iodonation of a cyclohexenone.

Original language	English
Pages (from-to)	9155-9158
Number of pages	4
Journal	Tetrahedron Letters
Volume	43
Issue number	50
DOIs	https://doi.org/10.1016/S0040-4039(02)02271-2
Publication status	Published - 2002 Dec 9
Externally published	Yes

Keywords

Diels-Alder reaction
Epoxyquinols A and B
Lipase
Resolution

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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abstract = "A practical total synthesis of both enantiomers of epoxyquinols A and B has been developed. Key reactions are the chromatography-free preparation of an iodolactone by using acryloyl chloride as dienophile in the Diels-Alder reaction of furan, the lipase-mediated kinetic resolution of a cyclohexenol derivative, and a modified procedure for α-iodonation of a cyclohexenone.",

keywords = "Diels-Alder reaction, Epoxyquinols A and B, Lipase, Resolution",

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T1 - A practical total synthesis of both enantiomers of epoxyquinols A and B

AU - Shoji, Mitsuru

AU - Kishida, Satoshi

AU - Takeda, Mitsuhiro

AU - Kakeya, Hideaki

AU - Osada, Hiroyuki

AU - Hayashi, Yujiro

PY - 2002/12/9

Y1 - 2002/12/9

N2 - A practical total synthesis of both enantiomers of epoxyquinols A and B has been developed. Key reactions are the chromatography-free preparation of an iodolactone by using acryloyl chloride as dienophile in the Diels-Alder reaction of furan, the lipase-mediated kinetic resolution of a cyclohexenol derivative, and a modified procedure for α-iodonation of a cyclohexenone.

AB - A practical total synthesis of both enantiomers of epoxyquinols A and B has been developed. Key reactions are the chromatography-free preparation of an iodolactone by using acryloyl chloride as dienophile in the Diels-Alder reaction of furan, the lipase-mediated kinetic resolution of a cyclohexenol derivative, and a modified procedure for α-iodonation of a cyclohexenone.

KW - Diels-Alder reaction

KW - Epoxyquinols A and B

KW - Lipase

KW - Resolution

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

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