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

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.

SUBMITTER: Han S

PROVIDER: S-EPMC3947030 | biostudies-literature | 2014 Jan

REPOSITORIES: biostudies-literature

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

Han Sunkyu S Morrison Karen C KC Hergenrother Paul J PJ Movassaghi Mohammad M

The Journal of organic chemistry 20131031 2

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, ...[more]

PMID: 24127681

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