title: Total synthesis of the eight diastereomers of the syn-anti-syn phytoprostanes F1 types I and II.
abstract: Syntheses of the eight enantiomerically pure diastereomers of the syn-anti-syn phytoprostanes F(1) types I and II are described starting from D- and L-glucose. Key steps include Wittig coupling, Horner Wadsworth Emmons (HWE) reactions, and enantioselective reduction of alpha,beta-unsaturated ketones.
authors.affiliation: UMR CNRS 5074, Université Montpellier I, Faculté de Pharmacie, 3e Etage-15, Avenue Charles Flahault, F-34093 Montpellier Cedex 05, France.
authors.forename: Siham
authors.initials: S
authors.lastname: El Fangour
authors.forename: Alexandre
authors.initials: A
authors.lastname: Guy
authors.forename: Valérie
authors.initials: V
authors.lastname: Despres
authors.forename: Jean-Pierre
authors.initials: JP
authors.lastname: Vidal
authors.forename: Jean-Claude
authors.initials: JC
authors.lastname: Rossi
authors.forename: Thierry
authors.initials: T
authors.lastname: Durand
mesh_terms: D002384:Catalysis; D003517:Cyclopentanes / Q000138:chemical synthesis*; D028441:F2-Isoprostanes / Q000138:chemical synthesis*; D005231:Fatty Acids, Unsaturated / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013237:Stereoisomerism
chemical_list: D003517:Cyclopentanes; D028441:F2-Isoprostanes; D005231:Fatty Acids, Unsaturated; D007202:Indicators and Reagents; C486066:phytoprostane F1