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.

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

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