Campus Units

Chemistry

Document Type

Article

Publication Version

Published Version

Publication Date

3-1995

Journal or Book Title

Journal of Organic Chemistry

Volume

60

Issue

5

First Page

1154

Last Page

1159

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

Included in

Chemistry Commons

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