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Synthesis of the Indolic Pentacyclic Core of Manadomanzamine A Following Biogenetically Based Strategies†

  1. Lok-Hang Yan1,
  2. Philippe Nuhant2,
  3. Isabelle Sinigaglia2,
  4. Yann Fromentin1,
  5. Christian Marazano2,‡,
  6. Bernard Delpech2,
  7. Erwan Poupon1

Article first published online: 4 JAN 2012

DOI: 10.1002/ejoc.201101133

Issue

European Journal of Organic Chemistry

European Journal of Organic Chemistry

Volume 2012, Issue 6, pages 1147–1157, February 2012

Additional Information

How to Cite

Yan, L.-H., Nuhant, P., Sinigaglia, I., Fromentin, Y., Marazano, C., Delpech, B. and Poupon, E. (2012), Synthesis of the Indolic Pentacyclic Core of Manadomanzamine A Following Biogenetically Based Strategies. Eur. J. Org. Chem., 2012: 1147–1157. doi: 10.1002/ejoc.201101133

Author Information

  1. 1

    Laboratoire de Pharmacognosie associé au CNRS, UMR 8076 (BioCIS), LabEx LERMIT, Université Paris-Sud, Faculté de Pharmacie, 5, rue Jean-Baptiste Clément, 92296 Châtenay-Malabry, France, Fax: +33-(0)1-46-83-53-99

  2. 2

    Institut de Chimie des Substances Naturelles, Centre de Recherche de Gif, CNRS, Avenue de la Terrasse, 91198 Gif-sur-Yvette CEDEX, France

  1. ‡

    Deceased November 12, 2008

  1. †

    Dedicated to the memory of François Tillequin

Publication History

  1. Issue published online: 13 FEB 2012
  2. Article first published online: 4 JAN 2012
  3. Manuscript Received: 1 AUG 2011

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Keywords:

  • Alkaloids;
  • Natural products;
  • Biomimetic synthesis;
  • Polycycles

Abstract

Manadomanzamine A is a complex alkaloid isolated from a marine sponge that shows promising biological activities. A biosynthetic hypothesis is proposed and is used as a guideline for biomimetic approaches to the pentacyclic indole nucleus of manadomanzamine A. The rich chemistry of reactive C5 units such as glutaconaldehydes or aminopentadienals was exploited towards this end.

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