A facile route to 3a,8a-dihydrofuro[2,3-b]benzofurans

Cedric W. Holzapfel; D. Bradley; G. Williams

doi:10.1016/0040-4020(95)00456-I

A facile route to 3a,8a-dihydrofuro[2,3-b]benzofurans

Cedric W. Holzapfel, D. Bradley, G. Williams

Chemical Sciences

University of Johannesburg

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

32 Citations (Scopus)

Abstract

Consecutive employment of palladium-catalysis and samanum(II)iodide-induced radical chemistry allows access to analogues of the ABC enol ether tricycle of aflatoxin B₁ (1). The Pd-assisted coupling of tubutylstannyl ethers of various 2-iodophenols with 2,5-diacetoxy-2,5-dihydrofuran (4) provided products that could be cyclised into 3a,8a-dihydrofuro [2,3-b]benzofurans using SmI₂. Elimination of an acetatosamarium species provides the requisite unsaturation _situ.

Original language	English
Pages (from-to)	8555-8564
Number of pages	10
Journal	Tetrahedron
Volume	51
Issue number	31
DOIs	https://doi.org/10.1016/0040-4020(95)00456-I
Publication status	Published - 31 Jul 1995

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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abstract = "Consecutive employment of palladium-catalysis and samanum(II)iodide-induced radical chemistry allows access to analogues of the ABC enol ether tricycle of aflatoxin B1 (1). The Pd-assisted coupling of tubutylstannyl ethers of various 2-iodophenols with 2,5-diacetoxy-2,5-dihydrofuran (4) provided products that could be cyclised into 3a,8a-dihydrofuro [2,3-b]benzofurans using SmI2. Elimination of an acetatosamarium species provides the requisite unsaturation situ.",

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AU - Bradley, D.

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Y1 - 1995/7/31

N2 - Consecutive employment of palladium-catalysis and samanum(II)iodide-induced radical chemistry allows access to analogues of the ABC enol ether tricycle of aflatoxin B1 (1). The Pd-assisted coupling of tubutylstannyl ethers of various 2-iodophenols with 2,5-diacetoxy-2,5-dihydrofuran (4) provided products that could be cyclised into 3a,8a-dihydrofuro [2,3-b]benzofurans using SmI2. Elimination of an acetatosamarium species provides the requisite unsaturation situ.

AB - Consecutive employment of palladium-catalysis and samanum(II)iodide-induced radical chemistry allows access to analogues of the ABC enol ether tricycle of aflatoxin B1 (1). The Pd-assisted coupling of tubutylstannyl ethers of various 2-iodophenols with 2,5-diacetoxy-2,5-dihydrofuran (4) provided products that could be cyclised into 3a,8a-dihydrofuro [2,3-b]benzofurans using SmI2. Elimination of an acetatosamarium species provides the requisite unsaturation situ.

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ER -

A facile route to 3a,8a-dihydrofuro[2,3-b]benzofurans

Abstract

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