Total Synthesis, Stereochemical Assignment, and Biological Activity of All Known (−)-Trigonoliimines
Name
Movassaghi_Total synthesis.pdf
Size
1.21 MB
Format
Adobe PDF
Checksum (MD5)
221c93c4a7e576dda825f8f189614acc
Author(s)
Han, Sunkyu
Morrison, Karen C.
Hergenrother, Paul J.
Movassaghi, Mohammad
Date Issued
October 2013
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
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.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
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DOI of Published Version
https://doi.org/10.1021/jo4020358
