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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