The Journal of organic chemistry

General, regiodefined access to α-substituted butenolides through metal− halogen exchange of 3-bromo-2-silyloxyfurans. Efficient synthesis of an anti-inflammatory …

J Boukouvalas, RP Loach

Index: Boukouvalas, John; Loach, Richard P. Journal of Organic Chemistry, 2008 , vol. 73, # 20 p. 8109 - 8112

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Citation Number: 58

Abstract

A variety of R-substituted butenolides were efficiently prepared from 3-bromo-2- triisopropylsilyloxyfuran via lithium-bromine exchange and in situ quench with carbon or heteroatom electrophiles. The inherent flexibility of this methodology is illustrated by a short and efficient synthesis of an anti-inflammatory marine natural product.