4.5 Article

Divergent Oxidative Couplings between Indoles and 2,3-Dihydroxybenzoic Acid Derivatives for the Biomimetic Synthesis of Voacalgine A and Bipleiophylline

Journal

SYNTHESIS-STUTTGART
Volume 50, Issue 21, Pages 4229-4242

Publisher

GEORG THIEME VERLAG KG
DOI: 10.1055/s-0036-1591910

Keywords

alkaloids; oxidative coupling; indole; catechol; bipleiophylline

Funding

  1. ANR [ANR-15-CE29-0001 'Mount Indole', ANR-12-JS07-0002 'CouPhIn']
  2. 'Fondation pour le developpement de la chimie des substances naturelles et ses applications
  3. sous l'egide de l'Academie des Sciences'
  4. Universite Paris- Sud
  5. CNRS

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The present feature article details our endeavors towards the synthesis of the highly intricate bisindole alkaloid bipleiophylline and its biosynthetic precursor voacalgine A: from the development of a divergent oxidative coupling between indole and dihydroxybenzoic acids, to the exploration of the chemical space from natural products and culminating in the biomimetic assembly of voacalgine A and bipleiophylline.

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