Campus Units

Chemistry

Document Type

Article

Publication Version

Published Version

Publication Date

6-1993

Journal or Book Title

Journal of American Chemical Society

Volume

115

Issue

13

First Page

5859

Last Page

5860

DOI

10.1021/ja00066a078

Abstract

Thequinone subunit is contained in a broad range of biologically important natural products.' This subunit is present in anticancer agents such as the anthracyclines, antibiotics such as the rifamycins, antifungal agents such as kalafungin, and antimidial agents such as frenolicin B.2 The latter two compounds are members of the pyranonaphthoquinone family. The diverse biological activity of quinones has led to the development of several new synthetic methods for quinones. A number of methods involving cycloadditions,3 carbanion-mediated annulations,4 and nucleophilic and electrophilic reactions5 have been reported. Among the pathways featuring a cycloaddition reaction, one of the most general methods for the regiospecific synthesis of substituted quinones was pioneered by Rapoport and others.6 This method involves the Diels-Alder reaction of a substituted quinone and is depicted below. The X group is usually chlorine or bromine, but nitriles and sulfoxides7 can also be employed.

Comments

Reprinted (adapted) with permission from Journal of American Chemical Society, 115(13); 5859-5860. Doi: 10.1021/ja00066a078. Copyright 1993 American Chemical Society.

Copyright Owner

American Chemical Society

Language

en

File Format

application/pdf

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