TY - JOUR
T1 - Total synthesis, stereochemical assignment, and biological activity of all known (-)-trigonoliimines
AU - Han, Sunkyu
AU - Morrison, Karen C.
AU - Hergenrother, Paul J.
AU - Movassaghi, Mohammad
PY - 2014/1/17
Y1 - 2014/1/17
N2 - 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.
AB - 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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U2 - 10.1021/jo4020358
DO - 10.1021/jo4020358
M3 - Article
C2 - 24127681
AN - SCOPUS:84896802062
SN - 0022-3263
VL - 79
SP - 473
EP - 486
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 2
ER -