Single-step formation of structurally defined bicyclic peptides via S(N)Ar cyclization

Org Lett. 2001 Apr 5;3(7):971-4.

Abstract

[structure: see text]. A solid-phase methodology for macrocyclization via an S(N)Ar reaction has been developed for the unambiguous formation of bicyclic peptidic compounds in a single cyclization step. The cyclization strategy involves the reaction of a 3,5-dihydroxybenzoyl group with two nitrofluorobenzoyl moieties. The symmetry of the dihydroxy aromatic ring results in a single product, and the remaining nitro groups are subsequently reduced to anilines and acylated.

MeSH terms

  • Bridged Bicyclo Compounds / chemical synthesis*
  • Bridged Bicyclo Compounds / chemistry
  • Chromatography, High Pressure Liquid
  • Cyclization
  • Drug Design
  • Humans
  • Hydroxybenzoates / chemistry
  • Molecular Structure
  • Peptides / chemical synthesis*
  • Peptides / chemistry

Substances

  • Bridged Bicyclo Compounds
  • Hydroxybenzoates
  • Peptides