Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 79, Issue 2, Pages 473-486Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo4020358
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Funding
- NIH-NIGMS [GM074825]
- University of Illinois
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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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