Synthesis of Biaryl‐Bridged Cyclic Peptides via Catalytic Oxidative Cross‐Coupling Reactions. Issue 12 (30th January 2020)

• Record Type: Journal Article
• Authors: Ben‐Lulu, Mor; Gaster, Eden; Libman, Anna; Pappo, Doron
• Is Part Of: Angewandte Chemie international edition. Volume 59:Issue 12(2020)
• Page Start: 4835
• Page End: 4839
• Publication Date: 2020-01-30
• Subjects: biaryls -- C–H activation -- cyclic peptides -- dityrosine -- oxidative cross-coupling; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201913305
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: Biaryl‐bridged cyclic peptides comprise an intriguing class of structurally diverse natural products with significant biological activity. Especially noteworthy are the antibiotics arylomycin and its synthetic analogue G0775, which exhibits potent activity against Gram‐negative bacteria. Herein, we present a simple, flexible, and reliable strategy based on activating‐group‐assisted catalytic oxidative coupling for assembling biaryl‐bridged cyclic peptides from natural amino acids. The synthetic approach was utilized for preparing a number of natural and unnatural biaryl‐bridged cyclic peptides, including arylomycin/G0775 and RP 66453 cyclic cores. Abstract : An activating‐group‐assisted oxidative cross‐coupling strategy for the assembly of biaryl‐bridged cyclic peptides from natural amino acids was developed for the synthesis of arylomycin/G0775 and RP 66453 cyclic cores.