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Total Synthesis of the Four Enantiomerically Pure Diasteroisomers of the Phytoprostanes E 1 Type II and of the 15-E 2t -Isoprostanes

2008; American Chemical Society; Volume: 73; Issue: 8 Linguagem: Inglês

10.1021/jo702455g

1520-6904

Edith Pinot, Alexandre Guy, Anaïs Fournial, Laurence Balas, Jean‐Claude Rossi, Thierry Durand,

Antioxidant Activity and Oxidative Stress

Syntheses of the four enantiomerically pure diastereoisomers of the phytoprostanes E1 type II and 15-E2t-isoprostanes (1−4) are described. The key steps included the preparation of the Freïmanis (±)-hydroxycyclopentenone 5, enzymatic resolution of this racemic hydroxycyclopentenone, Wittig and Horner−Wadsworth−Emmons (HWE) coupling reactions and finally enantioselective reductions.