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Communication | Regular issue | Vol 2, No. 5, 1974, pp.601-606
Published online, 1st January, 1970
DOI: 10.3987/R-1974-05-0601
A General Method for Alkylating Butenolides; Reduction of Products to 3-, 2,3-, and 3,4-Substituted Furans

S. William Pelletier,* Zoltan Djarmati, Ivan V. Micovic, and Stevan D. Lajsic

*Institute for Natural Products Research and Department of Chemistry, Chemistry Building, The University of Georgia, Chemistry Building, Athens Georgia 30602-2556, U.S.A.

Abstract

A simple method for the alkylation of butenolides is investigated. The method involves addition of appropriate diazo compounds to butenolides, followed by thermal decomposition and affords 4-, 3,4-, and 4,5-substituted γ-crotonolactones in high yields. Reduction of those products with DIBALH, provides the substituted furans in good to excellent yields.