Synthesis of the sulfonate analogue of seminolipid via Horner-Wadsworth-Emmons olefination

J Org Chem. 2010 Aug 6;75(15):5363-6. doi: 10.1021/jo1008788.

Abstract

The first synthesis of the sulfonate analogue of seminolipid, the main sulfoglycolipid in mammalian sperm, is reported. Installation of the sulfonate unit was accomplished by a quite unexplored strategy based on Horner-Wadsworth-Emmons olefination on a 3 '-keto-galactoside, followed by stereoselective double bond reduction.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkenes / chemistry*
  • Lipids / chemistry*
  • Magnetic Resonance Spectroscopy
  • Spectrometry, Mass, Electrospray Ionization
  • Sulfonic Acids / chemistry*

Substances

  • Alkenes
  • Lipids
  • Sulfonic Acids