Total Synthesis, Stereochemical Assignment, and Biological Activity of All Known (−)-Trigonoliimines

Author(s)
Han, Sunkyu; Morrison, Karen C.; Hergenrother, Paul J.; Movassaghi, Mohammad
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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.
Date issued
2013-10
URI
http://hdl.handle.net/1721.1/95510
Department
Massachusetts Institute of Technology. Department of Chemistry
Journal
Journal of Organic Chemistry
Publisher
American Chemical Society (ACS)
Citation
Han, Sunkyu, Karen C. Morrison, Paul J. Hergenrother, and Mohammad Movassaghi. “Total Synthesis, Stereochemical Assignment, and Biological Activity of All Known (−)-Trigonoliimines.” The Journal of Organic Chemistry 79, no. 2 (January 17, 2014): 473–486.
Version: Author's final manuscript
ISSN
0022-3263
1520-6904
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