Synthesis of modified carboxyl binding pockets of vancomycin and teicoplanin

M Bois-Choussy, L Neuville…

Index: Bois-Choussy, Michele; Neuville, Luc; Beugelmans, Rene; Zhu, Jieping Journal of Organic Chemistry, 1996 , vol. 61, # 26 p. 9309 - 9322

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Citation Number: 46

Abstract

Sixteen-membered macrocycle 3 and 16+ 14 bicyclic compound 4, incorporating a terminal primary hydroxyl group in the peptide sequence, have been designed and synthesized. The syntheses feature the use of an efficient cycloetherification based on an intramolecular SNAr reaction for the formation of biaryl ether bonds. Cyclization of linear tetrapeptide 30, prepared via a convergent [2+ 2] segment coupling between 26 and 29, gave macrocycle ...