Total synthesis of pacidamycin D by Cu(I)-catalyzed oxy enamide formation

Org Lett. 2011 Oct 7;13(19):5240-3. doi: 10.1021/ol202124b. Epub 2011 Sep 8.

Abstract

The first total synthesis of pacidamycin D, which is expected to be a good candidate as an antibacterial agent against P. aeruginosa, is described. The key elements of our approach feature an efficient and stereocontrolled construction of the Z-oxyvinyl iodide and copper-catalyzed cross-coupling with the tetrapeptide carboxamide.

MeSH terms

  • Catalysis
  • Copper / chemistry*
  • Molecular Structure
  • Peptides / chemistry*
  • Pyrimidine Nucleosides / chemistry*

Substances

  • Peptides
  • Pyrimidine Nucleosides
  • pacidamycin 1
  • Copper