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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ASJC Scopus subject areas

  • Organic Chemistry

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