Synthesis 2018; 50(21): 4229-4242
DOI: 10.1055/s-0036-1591910
feature
© Georg Thieme Verlag Stuttgart · New York

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

Natacha Denizot
a  Institut de Chimie Moléculaire et des Matériaux d’Orsay (ICMMO), Université Paris-Sud, Université Paris-Saclay CNRS, UMR 8182, 91405 Orsay Cedex, France
,
David Lachkar
b  Pharmacognosie et chimie des substances naturelles, UMR CNRS BioCIS 8076, Université Paris-Sud, Université Paris-Saclay, CNRS, 92290 Châtenay-Malabry, France   Email: Guillaume.vincent@u-psud.fr   Email: Laurent.evanno@u-psud.fr   Email: Erwan.poupon@u-psud.fr
,
Cyrille Kouklovsky
a  Institut de Chimie Moléculaire et des Matériaux d’Orsay (ICMMO), Université Paris-Sud, Université Paris-Saclay CNRS, UMR 8182, 91405 Orsay Cedex, France
,
Erwan Poupon*
b  Pharmacognosie et chimie des substances naturelles, UMR CNRS BioCIS 8076, Université Paris-Sud, Université Paris-Saclay, CNRS, 92290 Châtenay-Malabry, France   Email: Guillaume.vincent@u-psud.fr   Email: Laurent.evanno@u-psud.fr   Email: Erwan.poupon@u-psud.fr
,
Laurent Evanno*
b  Pharmacognosie et chimie des substances naturelles, UMR CNRS BioCIS 8076, Université Paris-Sud, Université Paris-Saclay, CNRS, 92290 Châtenay-Malabry, France   Email: Guillaume.vincent@u-psud.fr   Email: Laurent.evanno@u-psud.fr   Email: Erwan.poupon@u-psud.fr
,
Guillaume Vincent*
a  Institut de Chimie Moléculaire et des Matériaux d’Orsay (ICMMO), Université Paris-Sud, Université Paris-Saclay CNRS, UMR 8182, 91405 Orsay Cedex, France
› Author Affiliations
We gratefully acknowledge, the ANR (ANR-15-CE29-0001 ‘Mount Indole’ and ANR-12-JS07-0002 ‘CouPhIn’), the ‘Fondation pour le développement de la chimie des substances naturelles et ses applications; sous l’égide de l’Académie des Sciences’, the Université Paris- Sud and the CNRS for financial support.
Further Information

Publication History

Received: 07 December 2017

Accepted after revision: 08 January 2018

Publication Date:
06 February 2018 (online)

Published as part of the Special Section on the 26th French–Japanese Symposium on Medicinal and Fine Chemistry

Abstract

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.

Supporting Information

 
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