The synthesis of paleic acid, an antimicrobial agent effective against Mannheimia and Pasteurella, and its structurally related derivatives

Bioorg Med Chem Lett. 2010 Oct 1;20(19):5843-6. doi: 10.1016/j.bmcl.2010.07.115. Epub 2010 Aug 3.

Abstract

A synthetic route to paleic acid 1, antimicrobial agent effective against Mannheimia haemolytica and Pasteurella multocida, has been established. The absolute configuration of the secondary hydroxyl group was controlled by a catalytic asymmetric alkylation of an aldehyde using a chiral titanium sulfonamide complex and the cis double bond was installed using a Wittig reaction. This synthetic route was also applied to the preparation of structurally related analogs, which were used in structure-activity relationship studies for antibacterial activity.

MeSH terms

  • Anti-Bacterial Agents / chemical synthesis*
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / pharmacology
  • Mannheimia haemolytica / drug effects*
  • Microbial Sensitivity Tests
  • Oleic Acids / chemical synthesis*
  • Oleic Acids / chemistry
  • Oleic Acids / pharmacology
  • Pasteurella multocida / drug effects*
  • Stereoisomerism
  • Structure-Activity Relationship

Substances

  • Anti-Bacterial Agents
  • Oleic Acids
  • paleic acid