Two-step Hantzsch based macrocyclization approach for the synthesis of thiazole-containing cyclopeptides

J Org Chem. 2010 Nov 19;75(22):7939-41. doi: 10.1021/jo1016822. Epub 2010 Oct 29.

Abstract

Macrocyclization via an efficient high-yielding solid-phase intramolecular thioalkylation reaction is described. The reaction of S-nucleophiles with newly generated N-terminal 4-chloromethyl thiazoles led to the desired macrocyclization products 5 in high purities and good overall yields.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cyclization
  • Molecular Structure
  • Peptides, Cyclic / chemical synthesis*
  • Peptides, Cyclic / chemistry
  • Thiazoles / chemical synthesis*
  • Thiazoles / chemistry

Substances

  • Peptides, Cyclic
  • Thiazoles