First synthesis of caerulomycin B. A new synthesis of caerulomycin C

J Org Chem. 2002 May 17;67(10):3272-6. doi: 10.1021/jo010913r.

Abstract

Caerulomycins produced by Streptomyces caeruleus are bipyridinic molecules endowed with antibiotic properties. The first synthesis of caerulomycin B (1) as well as a new synthesis of caerulomycin C (2) are reported. Starting from 3-hydroxypyridine, the same methodology was used to prepare both compounds 1 and 2. Efficiently controlled reactions such as metalation to allow the synthesis of 2,6-diiodo-3,4-dialkoxypyridines, which are key intermediates, and further halogen-lithium exchange and cross-coupling to reach the targets molecules 1 and 2 have been developed.

MeSH terms

  • 2,2'-Dipyridyl / analogs & derivatives*
  • 2,2'-Dipyridyl / chemical synthesis*
  • Anti-Bacterial Agents / chemical synthesis*
  • Catalysis
  • Chemistry, Organic / methods*
  • Halogens / chemistry
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Pyridines / chemical synthesis
  • Pyridones / chemical synthesis
  • Streptomyces / chemistry*

Substances

  • Anti-Bacterial Agents
  • Halogens
  • Pyridines
  • Pyridones
  • caerulomycin B
  • caerulomycin C
  • 2,2'-Dipyridyl