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Article
Synthetic studies toward verrucarol. 1. Synthesis of the AB ring system
The Journal of Organic Chemistry
  • George A. Kraus, Iowa State University
  • Kevn Frazier, Iowa State University
Document Type
Article
Publication Version
Published Version
Publication Date
11-1-1980
DOI
10.1021/jo01312a003
Abstract

A synthetic route to the AB ring system of verrucarol is described. After two routes employing intramolecular cyclization failed, the Diels-Alder reaction of methyl coumalate and isoprene afforded bicyclic lactone 13. Transformation of 13 into hydroxy lactone 16 involved cuprate addition, hydroxylation, and oxidation. The conversion of 16 into desired keto alcohol 14 was accomplished by enol ether formation, reduction of the lactone and ester, and hydrolysis of the enol ether. The successful nine-step sequence proceeded in an overall yield of 7.9% from methyl coumalate.

Comments

Reprinted (adapted) with permission from The Journal of Organic Chemistry, 45(24); 4820-4825. Doi: 10.1021/jo01312a003. Copyright 1980 American Chemical Society.

Copyright Owner
American Chemical Society
Language
en
File Format
application/pdf
Citation Information
George A. Kraus and Kevn Frazier. "Synthetic studies toward verrucarol. 1. Synthesis of the AB ring system" The Journal of Organic Chemistry Vol. 45 Iss. 24 (1980) p. 4820 - 4825
Available at: http://works.bepress.com/george_kraus/204/