Convenient Synthesis of Polysubstituted 3-Iodofurans through the Tandem Ring-Opening/Cyclization Reaction of 1-Alkynyl-2,3-epoxy Alcohols

Shu-guang Wen; Wei-min Liu; Yong-min Liang

doi:10.1055/s-2007-990830

PAPER

Convenient Synthesis of Polysubstituted 3-Iodofurans through the Tandem Ring-Opening/Cyclization Reaction of 1-Alkynyl-2,3-epoxy Alcohols

Shu-guang Wen^a,b, Wei-min Liu^a, Yong-min Liang*^a,c
^a State Key Laboratory of Solid Lubrication, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000, P. R. of China
^b Graduate School of Chinese Academy of Sciences, Beijing 100039, P. R. of China
^c State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, P. R. of China
Fax: +86(931)8912582; e-Mail: liangym@lzu.edu.cn;

Abstract

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Abstract

A novel method for the synthesis of highly substituted iodine-containing furans has been developed by the cyclization of 1-(arylethynyl)-2,3-epoxy alcohols (1-aryl-4,5-epoxyalk-1-yn-3-ols) with alcohols as nucleophiles under very mild reaction conditions. The resulting iodine-containing furans can be readily elaborated to more complex products using known organopalladium chemistry.

Key word

iodofuran - tandem reaction - epoxide - electrophilic cyclization

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Referenzen

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