Synthetic studies toward verrucarol. 2. Synthesis of the AB ring system
Date
1980-11-01
Authors
Major Professor
Advisor
Committee Member
Journal Title
Journal ISSN
Volume Title
Publisher
Authors
Person
Kraus, George
University Professor Emeritus
Research Projects
Organizational Units
Organizational Unit
Journal Issue
Is Version Of
Versions
Series
Department
Chemistry
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.
Description
Keywords
Citation
DOI
Subject Categories
Copyright
Tue Jan 01 00:00:00 UTC 1980