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DOI: 10.1055/s-2003-41005
Synthesis of the Pyrrole-ImidazoleAlkaloids
Publication History
Publication Date:
07 August 2003 (online)
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.
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1 Introduction
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1.1 Alkaloid Economy
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1.2 Biosynthesis
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1.3 Biological Activity
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2 Reactivity of Partial Structures
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2.1 2-Aminoimidazole
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2.2 Pyrrole-2-carboxamide
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3 Non-Cyclized Pyrrole-Imidazole Alkaloids
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3.1 Starting from Imidazole
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3.2 Assembly of the Imidazole Portion
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4 Biomimetic Syntheses
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4.1 Cyclized Monomers
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4.2 Dimeric Pyrrole-Imidazole Alkaloids
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5 Non-Biomimetic Approaches
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5.1 Completed Syntheses
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5.2 Under Construction
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6 Cyclization Map
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7 Conclusion
Key words
alkaloids - diversity - imidazole - marinenatural products - pyrrole
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