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Issue 5, 2010
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Total synthesis of all (−)-agelastatin alkaloids

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Abstract

The pyrrole-imidazole family of marine alkaloids, derived from linear clathrodin-like precursors, constitutes a diverse array of structurally complex natural products. The bioactive agelastatins are members of this family that possess a tetracyclic molecular framework incorporating C4–C8 and C7–N12 bond connectivities. We provide a hypothesis for the formation of the unique agelastatin architecture that maximally exploits the intrinsic chemistry of plausible biosynthetic precursors. We report the concise enantioselective total syntheses of all known agelastatin alkaloids including the first total syntheses of agelastatins C, D, E, and F. Our gram-scale chemical synthesis of agelastatin A was inspired by our hypothesis for the biogenesis of the cyclopentane C-ring and required the development of new transformations including an imidazolone-forming annulation reaction and a carbohydroxylative trapping of imidazolones.

Graphical abstract: Total synthesis of all (−)-agelastatin alkaloids

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Publication details

The article was received on 02 Jul 2010, accepted on 20 Jul 2010 and first published on 16 Aug 2010


Article type: Edge Article
DOI: 10.1039/C0SC00351D
Citation: Chem. Sci., 2010,1, 561-566
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    Total synthesis of all (−)-agelastatin alkaloids

    M. Movassaghi, D. S. Siegel and S. Han, Chem. Sci., 2010, 1, 561
    DOI: 10.1039/C0SC00351D

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