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Synlett 2015; 26(04): 432-440
DOI: 10.1055/s-0034-1379495
DOI: 10.1055/s-0034-1379495
synpacts
The Quest for an Oxidative Coupling of Phenols and Indoles towards Benzofuroindolines: A Two-Stage Approach
Further Information
Publication History
Received: 12 September 2014
Accepted after revision: 18 October 2014
Publication Date:
09 December 2014 (online)
Abstract
The benzofuroindoline motif is found in several natural products and its biosynthesis is believed to be the oxidative coupling of phenols and indoles. A two-stage sequence has been developed to assemble these two units through the generation of electrophilic N-acetylindoles. A large number of benzofuroindolines were obtained by this strategy.
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Azonazine:
Bipleiophylline:
Voacalgine A:
Pleiocraline:
For a review, see:
Selected examples:
For the use of electrochemistry in lieu of iodine reagents, see:
For a review on electrophilic indole-derivatives, see:
For a review on dearomatization strategies of indoles, see: