Campus Units
Chemistry
Document Type
Article
Publication Version
Published Version
Publication Date
10-1983
Journal or Book Title
The Journal of Organic Chemistry
Volume
48
Issue
20
First Page
3439
Last Page
3444
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.
Copyright Owner
American Chemical Society
Copyright Date
1983
Language
en
File Format
application/pdf
Recommended Citation
Kraus, George A.; Cho, Hidetsura; Crowley, Steven; Roth, Bruce; Sugimoto, Hirokiko; and Prugh, Susan, "Phthalide annulation: the synthesis of kalafungin, pachybasin and chrysophanol" (1983). Chemistry Publications. 708.
https://lib.dr.iastate.edu/chem_pubs/708
Comments
Reprinted (adapted) with permission from The Journal of Organic Chemistry, 48(20); 3439-3444. Doi: 10.1021/jo00168a013. Copyright 1983 American Chemical Society.