Issue 95, 2012
From the journal:

Chemical Communications

Peptidic macrocyclization viapalladium-catalyzed chemoselective indole C-2 arylation†

Huijun Dong,a   Chris Limberakis,b   Spiros Liras,b   David Priceb  and  Keith James*a  

* Corresponding authors

a Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California, USA
E-mail: kjames@scripps.edu
Tel: +1 858 784 2507

b Pfizer Worldwide R&D, Eastern Point Road, Groton, Connecticut, USA

Abstract

A highly efficient macrocyclization reaction has been developed via the palladium-catalyzed C–H arylation of the side-chains of tryptophan with halophenyl-containing amino acids. This method allows for direct access to 15- to 25-membered biaryl macrocycles in 40–75% yield, at moderate concentration, with C–H arylation proceeding exclusively at the C-2 position of the tryptophan indole.

Graphical abstract: Peptidic macrocyclization via palladium-catalyzed chemoselective indole C-2 arylation

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Article information

DOI
https://doi.org/10.1039/C2CC36962A
Article type
Communication
Submitted
25 Sep 2012
Accepted
16 Oct 2012
First published
17 Oct 2012

Chem. Commun., 2012,48, 11644-11646

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Peptidic macrocyclization via palladium-catalyzed chemoselective indole C-2 arylation

H. Dong, C. Limberakis, S. Liras, D. Price and K. James, Chem. Commun., 2012, 48, 11644 DOI: 10.1039/C2CC36962A

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