New synthesis of (-)- and (+)-actinobolin from D-glucose

Satoshi Imuta; Shinya Ochiai; Miho Kuribayashi; Noritaka Chida

doi:10.1016/S0040-4039(03)01186-9

New synthesis of (-)- and (+)-actinobolin from D-glucose

Satoshi Imuta, Shinya Ochiai, Miho Kuribayashi, Noritaka Chida

Department of Applied Chemistry

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

13 Citations (Scopus)

Abstract

The total synthesis of (-)-actinobolin 2, an antipode of the natural product starting from D-glucose is described. A three-component coupling reaction of a functionalized cyclohexenone (+)-6, derived from D-glucose by way of Ferrier's carbocyclization, with vinyl cuprate and an aldehyde (R)-5 effectively constructed the carbon framework of 2 in a highly stereoselective manner. The formal synthesis of the natural enantiomer 1 from D-glucose was also achieved.

Original language	English
Pages (from-to)	5047-5051
Number of pages	5
Journal	Tetrahedron Letters
Volume	44
Issue number	27
DOIs	https://doi.org/10.1016/S0040-4039(03)01186-9
Publication status	Published - 2003 Jun 30

Keywords

Actinobolin
Carbohydrate
Ferrier's carbocyclization
Three-component coupling reaction

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4039(03)01186-9

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abstract = "The total synthesis of (-)-actinobolin 2, an antipode of the natural product starting from D-glucose is described. A three-component coupling reaction of a functionalized cyclohexenone (+)-6, derived from D-glucose by way of Ferrier's carbocyclization, with vinyl cuprate and an aldehyde (R)-5 effectively constructed the carbon framework of 2 in a highly stereoselective manner. The formal synthesis of the natural enantiomer 1 from D-glucose was also achieved.",

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AU - Imuta, Satoshi

AU - Ochiai, Shinya

AU - Kuribayashi, Miho

AU - Chida, Noritaka

PY - 2003/6/30

Y1 - 2003/6/30

N2 - The total synthesis of (-)-actinobolin 2, an antipode of the natural product starting from D-glucose is described. A three-component coupling reaction of a functionalized cyclohexenone (+)-6, derived from D-glucose by way of Ferrier's carbocyclization, with vinyl cuprate and an aldehyde (R)-5 effectively constructed the carbon framework of 2 in a highly stereoselective manner. The formal synthesis of the natural enantiomer 1 from D-glucose was also achieved.

AB - The total synthesis of (-)-actinobolin 2, an antipode of the natural product starting from D-glucose is described. A three-component coupling reaction of a functionalized cyclohexenone (+)-6, derived from D-glucose by way of Ferrier's carbocyclization, with vinyl cuprate and an aldehyde (R)-5 effectively constructed the carbon framework of 2 in a highly stereoselective manner. The formal synthesis of the natural enantiomer 1 from D-glucose was also achieved.

KW - Actinobolin

KW - Carbohydrate

KW - Ferrier's carbocyclization

KW - Three-component coupling reaction

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

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ER -

New synthesis of (-)- and (+)-actinobolin from D-glucose

Abstract

Keywords

ASJC Scopus subject areas

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