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Keywords:

  • aldol reaction;
  • isoprostanes;
  • phospholipids;
  • phosphorylcholine;
  • total synthesis
Thumbnail image of graphical abstract

The two possible diastereomers of 5,6-epoxyisoprostane A2 were synthesized efficiently through aldol condensations of a substituted cyclopentenone and the corresponding epoxyaldehydes (see picture). The relative configurations of the products were assigned by comparing their 1H NMR spectra with literature data. Condensation of the epoxyisoprostane A2 with lysophosphorylcholine (lyso-PC) then furnished the title lipid.