Synthesis of the pyrrolidinone core of KSM-2690 B

Org Lett. 2007 Feb 1;9(3):421-4. doi: 10.1021/ol062705x.

Abstract

[reaction: see text] The first synthesis of the pyrrolidinone core of the polyene beta-lactone antibiotic KSM-2690 B is described. An ammonia-free Birch reductive aldol reaction utilizing acetaldehyde is one of the key steps, together with a ruthenium-catalyzed alkene isomerization reaction.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetaldehyde / chemistry
  • Alkenes / chemistry
  • Ammonia / chemistry
  • Anti-Bacterial Agents / chemistry*
  • Catalysis
  • Isomerism
  • Lactones / chemistry*
  • Models, Chemical
  • Oxazoles / chemistry*
  • Oxidation-Reduction
  • Pyrrolidinones / chemical synthesis*
  • Rhodium / chemistry
  • Spiro Compounds / chemistry*

Substances

  • Alkenes
  • Anti-Bacterial Agents
  • Lactones
  • Oxazoles
  • Pyrrolidinones
  • Spiro Compounds
  • diffusomycin
  • Ammonia
  • Rhodium
  • Acetaldehyde