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Chemical communications (Cambridge, England)

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


PMID 23096995

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.

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48157 Indole solution, 2000 μg/mL in methanol, certified reference material