6. Biomimetic Synthesis of Manzamine Alkaloids

  1. Prof. Dr. Erwan Poupon2 and
  2. Dr. Bastien Nay3
  1. Romain Duval1 and
  2. Prof. Dr. Erwan Poupon2

Published Online: 21 APR 2011

DOI: 10.1002/9783527634606.ch6

Biomimetic Organic Synthesis

Biomimetic Organic Synthesis

How to Cite

Duval, R. and Poupon, E. (2011) Biomimetic Synthesis of Manzamine Alkaloids, in Biomimetic Organic Synthesis (eds E. Poupon and B. Nay), Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, Germany. doi: 10.1002/9783527634606.ch6

Editor Information

  1. 2

    Université Paris-Sud 11, Faculté du Pharmacie, 5, rue Jean-Baptiste Clément, 92260 Châtenay-Malabry, France

  2. 3

    Muséum National d'Histoire Naturelle, Unité Molécules de Communication et Adaptation des Micro-organismes associée au CNRS (UMR 7245), 57 rue Cuvier, 75005 Paris, France

Author Information

  1. 1

    Institut de Recherche pour le Dévelopement, UMR 152, Faculté des Sciences Pharmaceutiques, 118 Route de Narbonne, 31062 Toulouse, France

  2. 2

    Université Paris-Sud 11, Faculté du Pharmacie, 5, rue Jean-Baptiste Clément, 92260 Châtenay-Malabry, France

  1. In memory of the late Dr Christian Marazano whose creativity and humanity will always inspire us.

Publication History

  1. Published Online: 21 APR 2011
  2. Published Print: 20 APR 2011

ISBN Information

Print ISBN: 9783527325801

Online ISBN: 9783527634606

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Keywords:

  • Baldwin's hypothesis;
  • biomimetic synthesis;
  • manzamine alkaloids;
  • malondialdehyde;
  • pyridinium marine sponge alkaloids

Summary

This chapter contains sections titled:

  • Introduction

  • Two Complementary Hypotheses: An “Acrolein Scenario” and a “Malondialdehyde Scenario”

  • Biomimetic Synthesis of Pyridinium Marine Sponge Alkaloids

  • Development of Baldwin's Hypothesis: From Cyclostellettamines to Keramaphidin-Type Alkaloids

  • “Malondialdehyde Scenario:” A Modified Hypothesis Placing Aminopentadienals as Possible Precursors of Manzamine Alkaloids

  • Testing the Modified Hypothesis in the Laboratory

  • Biomimetic Approaches toward Other Manzamine Alkaloids

  • A Biomimetic Tool-Box for the Synthesis of Manzamine Alkaloids: Glutaconaldehydes and Aminopentadienals

  • Biosynthesis of Manzamine Alkaloids: Towards a Universal Scenario

  • Total Syntheses of Manzamine-Type Alkaloids

  • Conclusion

  • References