Construction of macrocyclic thiodepsipeptides: synthesis of a nosiheptide 'southern hemisphere' model system

Chem Commun (Camb). 2008 Feb 7:(5):591-3. doi: 10.1039/b715644h. Epub 2007 Nov 23.

Abstract

A 20-membered macrocyclic thiodepsipeptide has been synthesized as a model for the southern hemisphere of nosiheptide, the key steps being assembly of an acyclic precursor by amide coupling of indole and thiazole fragments followed by formation of the thiolactone in the macrocyclization step.

MeSH terms

  • Cyclization
  • Depsipeptides / chemical synthesis*
  • Depsipeptides / chemistry
  • Macrocyclic Compounds / chemical synthesis*
  • Macrocyclic Compounds / chemistry
  • Magnetic Resonance Spectroscopy / methods
  • Models, Chemical*
  • Molecular Conformation
  • Stereoisomerism
  • Sulfhydryl Compounds / chemical synthesis*
  • Sulfhydryl Compounds / chemistry
  • Thiazoles / chemical synthesis
  • Thiazoles / chemistry

Substances

  • Depsipeptides
  • Macrocyclic Compounds
  • Sulfhydryl Compounds
  • Thiazoles
  • nosiheptide