title: Total Synthesis of the Four Enantiomerically Pure Diasteroisomers of the Phytoprostanes E1Type II and of the 15-E2t-Isoprostanes.
abstract: 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.
authors: Institut des Biomolécules Max Mousseron, IBMM, UMR CNRS 5247, Université Montpellier I, Université Montpellier II, Faculté de Pharmacie, 15. Av. Ch. Flahault, F-34093 Montpellier cedex 05, France.
authors: Edith
authors: E
authors: Pinot
authors: Alexandre
authors: A
authors: Guy
authors: Anais
authors: A
authors: Fournial
authors: Laurence
authors: L
authors: Balas
authors: Jean-Claude
authors: JC
authors: Rossi
authors: Thierry
authors: T
authors: Durand
mesh_terms: D003517:Cyclopentanes / Q000737:chemistry; D006859:Hydrogen / Q000737:chemistry; D028421:Isoprostanes / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D003517:Cyclopentanes; D028421:Isoprostanes; C007201:cyclopentanone; D006859:Hydrogen