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

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.

Key words

oxidative coupling - indole - dearomatization - phenol - benzo­furoindoline - bipleiophylline

• References


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