Stereostructure of a novel cytotoxic 18-membered macrolactone antibiotic FD-891

Org Lett. 2002 Oct 3;4(20):3383-6. doi: 10.1021/ol026518k.

Abstract

The absolute stereochemistry of FD-891, a novel cytotoxic 18-membered macrolactone antibiotic, was determined by a synthetic approach as well as X-ray diffraction of degradative derivatives. The absolute configuration of FD-891 turned out to be as shown above. The stable conformer of FD-891 was also discussed with respect to biological activity by comparison with the structurally related concanamycin A on the bases of molecular mechanics calculations. [structure: see text]

MeSH terms

  • Anti-Bacterial Agents / chemistry*
  • Anti-Bacterial Agents / toxicity*
  • Macrolides*
  • Magnetic Resonance Spectroscopy
  • Molecular Conformation
  • Molecular Structure
  • Stereoisomerism
  • X-Ray Diffraction

Substances

  • Anti-Bacterial Agents
  • Macrolides
  • FD 891
  • concanamycin A