Total Synthesis of 2-(5,6-Epoxyisoprostane A2)phosphorylcholine and Elucidation of the Relative Configuration of the Isoprostane Moiety


  • We thank NOF Corporation, Japan, for a generous supply of 1-palmitoyl lysophosphorylcholine. This work was supported by a Grant-in-Aid for Scientific Research from the Ministry of Education, Science, Sports, and Culture of Japan and the Sasakawa Scientific Research Grant from The Japan Science Society.


original image

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.