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. 2009 Jan 7:(1):104-6.
doi: 10.1039/b816989f. Epub 2008 Nov 11.

A microwave assisted intramolecular-furan-Diels-Alder approach to 4-substituted indoles

Filip Petronijevic  1 , Cody Timmons, Anthony Cuzzupe, Peter Wipf
Affiliations

A microwave assisted intramolecular-furan-Diels-Alder approach to 4-substituted indoles

Filip Petronijevic et al. Chem Commun (Camb). .

Abstract

The key steps of a versatile new protocol for the convergent synthesis of 3,4-disubstituted indoles are the addition of an alpha-lithiated alkylaminofuran to a carbonyl compound, a microwave-accelerated intramolecular Diels-Alder cycloaddition and an in situ double aromatization reaction.

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Figures

Fig. 1
Fig. 1
Representative synthetic and natural products with 4-substituted indole scaffolds (outlined in bold).
Scheme 1
Scheme 1
Proposed indole synthesis.
Scheme 2
Scheme 2
The preparation of furanyl stannane 10, and a typical transmetalation and aldehyde addition reaction.
See this image and copyright information in PMC

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