title: Peptidic macrocyclization via palladium-catalyzed chemoselective indole C-2 arylation.
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.
authors.affiliation: Department of Chemistry, The Scripps Research Institute, La Jolla, California 92037, USA.
authors.forename: Huijun
authors.initials: H
authors.lastname: Dong
authors.forename: Chris
authors.initials: C
authors.lastname: Limberakis
authors.forename: Spiros
authors.initials: S
authors.lastname: Liras
authors.forename: David
authors.initials: D
authors.lastname: Price
authors.forename: Keith
authors.initials: K
authors.lastname: James
mesh_terms: D002244:Carbon / Q000737:chemistry; D002384:Catalysis; D018360:Crystallography, X-Ray; D003500:Cyclization; D007211:Indoles / Q000737:chemistry*; D047028:Macrocyclic Compounds / Q000737:chemistry*; D008968:Molecular Conformation; D010165:Palladium / Q000737:chemistry*; D014364:Tryptophan / Q000737:chemistry
chemical_list: D007211:Indoles; D047028:Macrocyclic Compounds; D010165:Palladium; D002244:Carbon; C030374:indole; D014364:Tryptophan