Online article for Non-subscribers

Pay per view

Heterocycles has a pay-per-view service for Non-subscribers.
You will be able to directly purchase the full text article through PayPal.
Your purchased Paper can be downloaded after the payment is completed.
An e-mail will be sent the URL to download the paper.
If you have any questions, please contact:

Price: ¥ 4,400 (Yen only)
Period: This Article can be accessed for 7 days.

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.


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.