4.8 Article

Biomimetic Synthesis of the Antimalarial Flindersial Alkaloids

Journal

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 134, Issue 16, Pages 6936-6939

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ja301387k

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Funding

  1. Welch Foundation [E-1744]
  2. University of Houston

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A biomimetic strategy for the synthesis of the antimalarial flindersial alkaloids is described. Flinderoles A, B, and C, desmethylflinderole C, isoborreverine, and dimethylisoborreverine were all synthesized in three steps from tryptamine. The key step is an acid-promoted dimerization of the natural product borrerine. This approach is thought to mirror the biosynthesis of these compounds.

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