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

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

Research output: Contribution to journalArticlepeer-review

9 Scopus citations

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.

Original languageEnglish
Pages (from-to)4835-4839
Number of pages5
JournalAngewandte Chemie - International Edition
Volume59
Issue number12
DOIs
StatePublished - 16 Mar 2020

Keywords

  • C–H activation
  • biaryls
  • cyclic peptides
  • dityrosine
  • oxidative cross-coupling

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