Organocatalytic asymmetric syntheses of inthomycins A, B and C

Org Biomol Chem. 2012 Oct 28;10(40):8164-74. doi: 10.1039/c2ob26084k.

Abstract

The total syntheses of (+)-inthomycin A, (+)-inthomycin B and (-)-inthomycin C, the oxazole-triene antibiotics isolated from Streptomyces sp., have been accomplished via the highly enantio- and stereoselective construction of the C1-C7 (iododienyl)aldol units by taking advantage of a Cinchona alkaloid-catalyzed asymmetric β-lactone synthesis and their isomerisation-free Stille coupling with (E)-5-(3-(tributylstannyl)allyl)oxazole.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Bacterial Agents / chemical synthesis*
  • Anti-Bacterial Agents / chemistry
  • Catalysis
  • Cinchona Alkaloids / chemistry*
  • Fatty Acids, Unsaturated / chemical synthesis*
  • Fatty Acids, Unsaturated / chemistry
  • Molecular Structure
  • Oxazoles / chemical synthesis*
  • Oxazoles / chemistry
  • Stereoisomerism

Substances

  • Anti-Bacterial Agents
  • Cinchona Alkaloids
  • Fatty Acids, Unsaturated
  • Oxazoles
  • inthomycin A
  • inthomycin B
  • inthomycin C