Synthesis of DEFG ring of complestatin and chloropeptin I: highly atropdiastereoselective macrocyclization by intramolecular Suzuki-Miyaura reaction.
Palladium-catalyzed intramolecular Suzuki-Miyaura reaction of linear tripeptide (23) afforded the 16-membered DEFG ring of complestatin (3) in good yield with an excellent atropdiastereoselectivity. Acidic treatment of 3 triggers a stereospecific rearrangement leading to the corresponding DEFG ring 4 of chloropeptin I.
Jia
Yanxing
Y
Institut de Chimie des Substances Naturelles, CNRS, 91198 Gif-sur-Yvette Cedex, France.
Bois-Choussy
Michèle
M
Zhu
Jieping
J
D002384:Catalysis; D002733:Chlorophenols / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D008968:Molecular Conformation; D010165:Palladium / Q000737:chemistry; D010455:Peptides / Q000737:chemistry*; D010456:Peptides, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D002733:Chlorophenols; D010455:Peptides; D010456:Peptides, Cyclic; C090485:chloropeptin I; D010165:Palladium; C023490:complestatin