Direct synthesis of plasmenylcholine from allyl-substituted glycerols

J Org Chem. 2003 Aug 22;68(17):6760-6. doi: 10.1021/jo026826w.

Abstract

We report a new method for the facile preparation of plasmenylcholine via reaction of lithioalkoxy allyl intermediates with 1-iodoalkanes as the key step in the stereoselective formation of 1'-(Z)-alkenyl glyceryl ethers. The allyl anion intermediate is prepared by treating mono- or disiloxy-protected 1-allylglycerol precursors with s-BuLi at -65 to -80 degrees C. Subsequent addition of 1-iodoalkane solutions at low temperature gives moderate yields of gamma-coupled, Z-vinyl ethers as the major product and alpha-coupled product as the minor component. Several different preparative strategies for the total synthesis of plasmalogens are enabled by this simple transformation.

Publication types

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

MeSH terms

  • Glycerol / analogs & derivatives*
  • Glycerol / chemistry*
  • Indicators and Reagents
  • Magnetic Resonance Spectroscopy
  • Molecular Conformation
  • Plasmalogens / chemical synthesis*
  • Plasmalogens / chemistry

Substances

  • Indicators and Reagents
  • Plasmalogens
  • choline plasmalogens
  • Glycerol