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Article
Phthalide annulation: the synthesis of kalafungin, pachybasin and chrysophanol
The Journal of Organic Chemistry
  • George A. Kraus, Iowa State University
  • Hidetsura Cho, Iowa State University
  • Steven Crowley, Iowa State University
  • Bruce Roth, Iowa State University
  • Hirokiko Sugimoto, Iowa State University
  • Susan Prugh, Iowa State University
Document Type
Article
Publication Version
Published Version
Publication Date
10-1-1983
DOI
10.1021/jo00168a013
Abstract
The anions of %cyano- or 3-(pheny1thio)phthalide react with Michael acceptors to afford functionalized naphthydroquinones in good yield. The cyano and phenylthio groups function both as activating groups and as leaving groups. An alternative involves the use of protected o-(carboxymethy1)cyanohydrins. The use of phthalide anions in synthesis is exemplified by total syntheses of kalafungin, pachybasin, and chrysophanol. This methodolgy consititutes a direct and regiospecific approach to polycyclic systems.
Comments

Reprinted (adapted) with permission from The Journal of Organic Chemistry, 48(20); 3439-3444. Doi: 10.1021/jo00168a013. Copyright 1983 American Chemical Society.

Copyright Owner
American Chemical Society
Language
en
File Format
application/pdf
Citation Information
George A. Kraus, Hidetsura Cho, Steven Crowley, Bruce Roth, et al.. "Phthalide annulation: the synthesis of kalafungin, pachybasin and chrysophanol" The Journal of Organic Chemistry Vol. 48 Iss. 20 (1983) p. 3439 - 3444
Available at: http://works.bepress.com/george_kraus/80/