Literature DB >> 24127681

Total synthesis, stereochemical assignment, and biological activity of all known (-)-trigonoliimines.

Sunkyu Han1, Karen C Morrison, Paul J Hergenrother, Mohammad Movassaghi.   

Abstract

A full account of our concise and enantioselective total syntheses of all known (-)-trigonoliimine alkaloids is described. Our retrobiosynthetic analysis of these natural products enabled identification of a single bistryptamine precursor as a precursor to all known trigonoliimines through a sequence of transformations involving asymmetric oxidation and reorganization. Our enantioselective syntheses of these alkaloids enabled the revision of the absolute stereochemistry of (-)-trigonoliimines A, B, and C. We report that trigonoliimines A, B, C and structurally related compounds showed weak anticancer activities against HeLa and U-937 cells.

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Year:  2013        PMID： 24127681      PMCID： PMC3947030          DOI： 10.1021/jo4020358

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


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