Base-dependent formation of cis and trans olefins and their application in the synthesis of 5-oxo-ETE receptor antagonists

Bioorg Med Chem Lett. 2014 Aug 1;24(15):3385-8. doi: 10.1016/j.bmcl.2014.05.090. Epub 2014 Jun 4.

Abstract

5-Oxo-ETE is the most potent eosinophil chemoattractant among lipid mediators. We have developed two 5-oxo-ETE receptor antagonists. In the course of the work, we have developed a procedure to selectively introduce a cis and trans double bond in an alkyl side chain. Reacting indolecarboxaldehydes with alkyl ylides using the Li base affords the trans olefins, whereas using the K base yields the cis olefins.

Keywords: 5-Oxo-ETE; Antagonist; Indolecarboxaldehyde; KHMDS; LiHMDS; Wittig reaction.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Alkenes / chemical synthesis
  • Alkenes / chemistry
  • Alkenes / pharmacology*
  • Molecular Structure
  • Receptors, Eicosanoid / antagonists & inhibitors*
  • Stereoisomerism
  • Structure-Activity Relationship

Substances

  • Alkenes
  • Receptors, Eicosanoid