Synthesis of the Pyrrole-ImidazoleAlkaloids

Holger Hoffmann; Thomas Lindel

doi:10.1055/s-2003-41005

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Synthesis 2003(12): 1753-1783
DOI: 10.1055/s-2003-41005

REVIEW

Synthesis of the Pyrrole-ImidazoleAlkaloids

Holger Hoffmann^a, Thomas Lindel*^b
^a Aventis Pharma Deutschland GmbH, Natural Products Research, 65926 Frankfurt,Germany
^b Ludwig-Maximilians-University, Department of Chemistry, 81377 Munich,Germany
Fax: +49(89)218077734; e-Mail: thomas.lindel@cup.uni-muenchen.de;

Further Information

Publication History

Received 12 February 2003
Publication Date:
07 August 2003 (online)

Abstract
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Abstract

This review article gives a detailed account on the chemistryof the pyrrole-imidazole alkaloids from marine sponges. The pyrrole-imidazolealkaloids share a key building block, oroidin being the underlyingstructural motif of a diverse range of exclusively marine alkaloids.After outlining the reactivity of 2-amino-4(5)-vinylimidazoles,biomimetic and non-biomimetic total syntheses of the non-cyclized,cyclized, and ‘dimerized’ pyrrole-imidazole alkaloidsdeveloped over the past 30 years are discussed in a comprehensivemanner. Beyond the identified pyrrole-imidazole alkaloids the theoreticalcyclization map based on oroidin contains many white spots and therebyopportunities to assemble novel pyrrole-imidazole alkaloids notobserved in nature before.

1 Introduction
1.1 Alkaloid Economy
1.2 Biosynthesis
1.3 Biological Activity
2 Reactivity of Partial Structures
2.1 2-Aminoimidazole
2.2 Pyrrole-2-carboxamide
3 Non-Cyclized Pyrrole-Imidazole Alkaloids
3.1 Starting from Imidazole
3.2 Assembly of the Imidazole Portion
4 Biomimetic Syntheses
4.1 Cyclized Monomers
4.2 Dimeric Pyrrole-Imidazole Alkaloids
5 Non-Biomimetic Approaches
5.1 Completed Syntheses
5.2 Under Construction
6 Cyclization Map
7 Conclusion

Key words

alkaloids - diversity - imidazole - marinenatural products - pyrrole

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