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Abstracts of Congress of Heterocyclic Chemistry | Regular issue | Vol 14, No. 10, 1980, pp.1703-1708
Published online, 1st January, 1970
DOI: 10.3987/R-1980-10-1703
Furan Synthesis

Ernest Wenkert*

*Department of Chemistry, Rice University, Houston, Texas 77251, U.S.A.

Abstract

The use of dimethyl diazomalonate in copper-catalyzed cyclopropanations of enol ethers led to intermediates readily convertible into β-methylfuran, α-methylene-γ-lactone and β-methylene-γ-lactone units common among terpene structures and to a synthesis of menthofuran. The copper-induced interaction of enol ethers with ethyl diazopyruvate yielded oxydihydrofuroic esters from which α-furoic acids, furans and the common α-isopropylfuran terpene structure could be constructed. A similar reaction of diazopyruvic ester with acetylenes produced α-furoates directly. The Fétizon oxidation of β-oxycyclopropyl carbinols has been shown to give oxydihydrofurans, an observation on which another menthofuran synthesis was based. The copper-assisted decomposition of diazobiacetyl monoketal in n-butyl vinyl ether afforded a cyclopropane whose treatment with methanolic acid afforded veratrole. This unusual benzene ring construction was utilized in a new synthesis of hydrourushiol.