jo4020358_si_001.pdf (1.19 MB)
Total Synthesis, Stereochemical Assignment, and Biological Activity of All Known (−)-Trigonoliimines
journal contribution
posted on 2015-12-17, 00:17 authored by Sunkyu Han, Karen
C. Morrison, Paul J. Hergenrother, Mohammad MovassaghiA 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.