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Article
Synthetic studies toward verrucarol. 2. Synthesis of the AB ring system
The Journal of Organic Chemistry
  • George A. Kraus, Iowa State University
  • Bruce Roth, Iowa State University
Document Type
Article
Publication Version
Published Version
Publication Date
11-1-1980
DOI
10.1021/jo01312a004
Abstract
A route to the AB ring system of verrucarol is described. The successful scheme involved the formation of the A ring by a boron triacetate catalyzed Diels-Alder reaction. The second ring can be appended by an intramolecular Knoevenagel reaction to afford lactone 12b. This lactone could be converted into the desired keto alcohol 3b by reduction of the lactone and nitrile followed by an oxidation and Curtius degradation.
Comments

Reprinted (adapted) with permission from The Journal of Organic Chemistry, 45(24); 4825-4830. Doi: 10.1021/jo01312a004. Copyright 1980 American Chemical Society.

Copyright Owner
American Chemical Society
Language
en
File Format
application/pdf
Citation Information
George A. Kraus and Bruce Roth. "Synthetic studies toward verrucarol. 2. Synthesis of the AB ring system" The Journal of Organic Chemistry Vol. 45 Iss. 24 (1980) p. 4825 - 4830
Available at: http://works.bepress.com/george_kraus/119/