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Article
Synthetic Routes to Pyrroloiminoquinone Alkaloids. A Direct Synthesis of Makaluvamine C
The Journal of Organic Chemistry
  • George A. Kraus, Iowa State University
  • Natesan Selvakumar, Iowa State University
Document Type
Article
Publication Version
Published Version
Publication Date
11-26-1998
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
Citation Information
George A. Kraus and Natesan Selvakumar. "Synthetic Routes to Pyrroloiminoquinone Alkaloids. A Direct Synthesis of Makaluvamine C" The Journal of Organic Chemistry Vol. 63 Iss. 26 (1998) p. 9846 - 9849
Available at: http://works.bepress.com/george_kraus/114/