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General, Regiodefined Access to α-Substituted Butenolides through Metal-Halogen Exchange of 3-Bromo-2-silyloxyfurans. Efficient Synthesis of an Anti-inflammatory Gorgonian Lipid

John Boukouvalas* and Richard P. Loach

*Département de Chimie, Université Laval, Quebec City, Quebec G1K 7P4, Canada, Email: john.boukouvalaschm.ulaval.ca

J. Boukouvalas, R. P. Loach, J. Org. Chem., 2008, 73, 8109-8112.

DOI: 10.1021/jo8015924 (free Supporting Information)


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Abstract

Various α-substituted butenolides were efficiently prepared from 3-bromo-2-triisopropylsilyloxyfuran via lithium-bromine exchange and subsequent derivatization with carbon or heteroatom electrophiles. A short and efficient synthesis of an anti-inflammatory lipid, isolated from a marine gorgonian, is described.

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gorgonian lipid



Key Words

Butenolides


ID: J42-Y2008-3140