A total synthesis of (+)-eremantholide A

Ken ichi Takao; Hiroshi Ochiai; Takahiko Hashizuka; Hirokazu Koshimura; Kin ichi Tadano; Seiichiro Ogawa

doi:10.1016/0040-4039(95)00066-L

A total synthesis of (+)-eremantholide A

Ken ichi Takao, Hiroshi Ochiai, Takahiko Hashizuka, Hirokazu Koshimura, Kin ichi Tadano, Seiichiro Ogawa

Department of Applied Chemistry

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

23 Citations (Scopus)

Abstract

Stereoselective and enantiospecific total synthesis of (+)-eremantholide A (1) is described. The present total synthesis features 1) regio- and stereoselective radical carbocyclization of D-glucose-derived γ-lactone7, and 2) a nine-membered ring formation by the coupling reaction of bicyclic triflate18 and known furanone19 followed by a vinylogous aldol reaction.

Original language	English
Pages (from-to)	1487-1490
Number of pages	4
Journal	Tetrahedron Letters
Volume	36
Issue number	9
DOIs	https://doi.org/10.1016/0040-4039(95)00066-L
Publication status	Published - 1995 Feb 27

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/0040-4039(95)00066-L

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title = "A total synthesis of (+)-eremantholide A",

abstract = "Stereoselective and enantiospecific total synthesis of (+)-eremantholide A (1) is described. The present total synthesis features 1) regio- and stereoselective radical carbocyclization of D-glucose-derived γ-lactone7, and 2) a nine-membered ring formation by the coupling reaction of bicyclic triflate18 and known furanone19 followed by a vinylogous aldol reaction.",

author = "Takao, {Ken ichi} and Hiroshi Ochiai and Takahiko Hashizuka and Hirokazu Koshimura and Tadano, {Kin ichi} and Seiichiro Ogawa",

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AU - Takao, Ken ichi

AU - Ochiai, Hiroshi

AU - Hashizuka, Takahiko

AU - Koshimura, Hirokazu

AU - Tadano, Kin ichi

AU - Ogawa, Seiichiro

PY - 1995/2/27

Y1 - 1995/2/27

N2 - Stereoselective and enantiospecific total synthesis of (+)-eremantholide A (1) is described. The present total synthesis features 1) regio- and stereoselective radical carbocyclization of D-glucose-derived γ-lactone7, and 2) a nine-membered ring formation by the coupling reaction of bicyclic triflate18 and known furanone19 followed by a vinylogous aldol reaction.

AB - Stereoselective and enantiospecific total synthesis of (+)-eremantholide A (1) is described. The present total synthesis features 1) regio- and stereoselective radical carbocyclization of D-glucose-derived γ-lactone7, and 2) a nine-membered ring formation by the coupling reaction of bicyclic triflate18 and known furanone19 followed by a vinylogous aldol reaction.

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

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ER -

A total synthesis of (+)-eremantholide A

Abstract

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