Total synthesis of the four enantiomerically pure diasteroisomers of the phytoprostanes E-1 type II and of the 15-E-2t-isoprostanes

摘要

Syntheses of the four enantionterically pure diastereoisomers of the phytoprostanes E-1 type II and 15-E-2t-isoprostanes (1-4) are described. The key steps included the preparation of the Freimanis (+/-)-hydroxycyclopentenone 5, enzymatic resolution of this racemic hydroxycyclopentenone, Wittig and Horner-Wadsworth-Emmons (HWE) coupling reactions and finally enantioselective reductions.