Total synthesis, stereochemical assignment, and biological activity of all known (-)-trigonoliimines

Sunkyu Han, Karen C. Morrison, Paul J. Hergenrother, Mohammad Movassaghi

Research output: Contribution to journalArticle

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.

Original languageEnglish (US)
Pages (from-to)473-486
Number of pages14
JournalJournal of Organic Chemistry
Volume79
Issue number2
DOIs
StatePublished - Jan 17 2014

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Bioactivity
Alkaloids
Stereochemistry
Biological Products
Oxidation
trigonoliimine A

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Total synthesis, stereochemical assignment, and biological activity of all known (-)-trigonoliimines. / Han, Sunkyu; Morrison, Karen C.; Hergenrother, Paul J.; Movassaghi, Mohammad.

In: Journal of Organic Chemistry, Vol. 79, No. 2, 17.01.2014, p. 473-486.

Research output: Contribution to journalArticle

Han, Sunkyu ; Morrison, Karen C. ; Hergenrother, Paul J. ; Movassaghi, Mohammad. / Total synthesis, stereochemical assignment, and biological activity of all known (-)-trigonoliimines. In: Journal of Organic Chemistry. 2014 ; Vol. 79, No. 2. pp. 473-486.
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