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

Sunkyu Han | Zendy; Karen Morrison | Zendy; Paul J. Hergenrother | Zendy; Mohammad Movassaghi | Zendy

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

Author(s) -

Sunkyu Han,

Karen Morrison,

Paul J. Hergenrother,

Mohammad Movassaghi

Publication year - 2013

Publication title -

the journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.2

H-Index - 228

eISSN - 1520-6904

pISSN - 0022-3263

DOI - 10.1021/jo4020358

Subject(s) - enantioselective synthesis , chemistry , total synthesis , hela , stereochemistry , sequence (biology) , stereoisomerism , combinatorial chemistry , organic chemistry , molecule , biochemistry , catalysis , in vitro

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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