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Article
Direct Total Syntheses of Frenolicin B and Kalafungin via Highly Regioselective Diels-Alder Reactions
Journal of Organic Chemistry
  • George A. Kraus, Iowa State University
  • Jun Li, Iowa State University
  • Mark S. Gordon, Iowa State University
  • Jan H. Jensen, Iowa State University
Document Type
Article
Disciplines
Publication Version
Published Version
Publication Date
3-1-1995
DOI
10.1021/jo00110a017
Abstract

Frenolicin B, an anticoccidial agent, has been synthesized in six steps from ketone 3. Racemic kalafungin, an antifungal agent, has been synthesized in five steps. The key step in both syntheses, a regioselective Diels-Alder reaction, proceeds with complete regiocontrol and in excellent yield. One rationale for the remarkable stereocontrol is that the lactone ring induces ring-puckering in the quinone subunit which, in consort with electrostatic repulsion, contributes to the regioselectivity.

Comments

Reprinted (adapted) with permission from Journal of Organic Chemistry 60 (1995): 1154, doi:10.1021/jo00110a017. Copyright 1995 American Chemical Society.

Copyright Owner
American Chemical Society
Language
en
File Format
application/pdf
Citation Information
George A. Kraus, Jun Li, Mark S. Gordon and Jan H. Jensen. "Direct Total Syntheses of Frenolicin B and Kalafungin via Highly Regioselective Diels-Alder Reactions" Journal of Organic Chemistry Vol. 60 Iss. 5 (1995) p. 1154 - 1159
Available at: http://works.bepress.com/george_kraus/50/