Synthesis 2018; 50(24): 4823-4828
DOI: 10.1055/s-0036-1592002
paper
© Georg Thieme Verlag Stuttgart · New York

N-Iodosuccinimide-Mediated Oxidative Coupling of Indoles and Phenols: A Synthetic Study toward the Benzofuroindoline Moiety of Bipleiophylline

Natacha Denizot
Institut de Chimie Moléculaire et des Matériaux d’Orsay (ICMMO), Université Paris-Sud, Université Paris-Saclay, CNRS, UMR 8182, 91405 Orsay Cedex, France   Email: Guillaume.vincent@u-psud.fr
,
Régis Guillot
Institut de Chimie Moléculaire et des Matériaux d’Orsay (ICMMO), Université Paris-Sud, Université Paris-Saclay, CNRS, UMR 8182, 91405 Orsay Cedex, France   Email: Guillaume.vincent@u-psud.fr
,
Cyrille Kouklovsky
Institut de Chimie Moléculaire et des Matériaux d’Orsay (ICMMO), Université Paris-Sud, Université Paris-Saclay, CNRS, UMR 8182, 91405 Orsay Cedex, France   Email: Guillaume.vincent@u-psud.fr
,
Institut de Chimie Moléculaire et des Matériaux d’Orsay (ICMMO), Université Paris-Sud, Université Paris-Saclay, CNRS, UMR 8182, 91405 Orsay Cedex, France   Email: Guillaume.vincent@u-psud.fr
› Author Affiliations
We gratefully acknowledge the ‘Fondation pour le développement de la chimie des substances naturelles et ses applications; sous l’égide de l’Académie des Sciences’ for a Ph.D. fellowship to N.D., the ANR (ANR-15-CE29-0001, ‘Mount Indole’; ANR-12-JS07-0002, ‘CouPhIn’), Université Paris-Sud and the CNRS for financial support.
Further Information

Publication History

Received: 14 February 2018

Accepted after revision: 03 April 2018

Publication Date:
08 May 2018 (online)

Dedicated to Prof. Marco A. Ciufolini

Abstract

We report our efforts to apply an N-iodosuccinimide-mediated dearomative oxidative coupling of indoles and phenols to benzo­furoindoline-containing polycyclic scaffolds related to the natural product bipleiophylline. Suitable conditions from N-substituted indoles are developed and applied to the synthesis of a hexacyclic model starting from a tetracyclic ABCE precursor.

Supporting Information

 
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