Synthesis of Biaryl-Bridged Cyclic Peptides via Catalytic Oxidative Cross-Coupling Reactions.

Mor Ben-Lulu, Eden Gaster, Anna Libman, Doron Pappo

Angewandte Chemie (International ed. in English) 2020 Mar 16

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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. © 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Citation

Mor Ben-Lulu, Eden Gaster, Anna Libman, Doron Pappo. Synthesis of Biaryl-Bridged Cyclic Peptides via Catalytic Oxidative Cross-Coupling Reactions. Angewandte Chemie (International ed. in English). 2020 Mar 16;59(12):4835-4839