Campus Units

Chemistry

Document Type

Article

Publication Version

Published Version

Publication Date

11-26-1998

Journal or Book Title

The Journal of Organic Chemistry

Volume

63

Issue

26

First Page

9846

Last Page

9849

DOI

10.1021/jo981547n

Abstract

Makaluvamine C is a pyrroloiminoquinone which has been isolated from marine sponges. This molecule has been synthesized in 13 steps from p-anisidine. The key steps in this synthesis include an intramolecular nucleophilic aromatic substitution mediated by potassiumtert-butoxide, the selective reduction of a dinitro ester using catalytic hydrogenation, and the novel use of Fremy's salt to synthesize an iminoquinone from an amino phenol. The synthesis of makaluvamine C has been achieved from p-anisidine in 13.1% overall yield.

Comments

Reprinted (adapted) with permission from The Journal of Organic Chemistry, 63(26); 9846-9849. doi: 10.1021/jo981547n. Copyright 1998 American Chemical Society.

Copyright Owner

American Chemical Society

Language

en

File Format

application/pdf

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