Total synthesis of all (−)-agelastatin alkaloids
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Movassaghi_Total Synthesis of.pdf
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Author(s)
Movassaghi, Mohammad
Siegel, Dustin S.
Han, Sunkyu
Date Issued
August 2010
Journal
Chemical Science
Publisher
Royal Society of Chemistry, The
Citation
Movassaghi, Mohammad, Dustin S. Siegel, and Sunkyu Han. “Total synthesis of all (−)-agelastatin alkaloids.” Chemical Science 1, no. 5 (2010): 561.
Version
Author's final manuscript
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.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
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Creative Commons Attribution-Noncommercial-Share Alike 3.0
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DOI of Published Version
https://doi.org/10.1039/c0sc00351d
