Total synthesis of the eight diastereomers of the syn-anti-syn phytoprostanes F1 types I and II.
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.
El Fangour
Siham
S
UMR CNRS 5074, Université Montpellier I, Faculté de Pharmacie, 3e Etage-15, Avenue Charles Flahault, F-34093 Montpellier Cedex 05, France.
Guy
Alexandre
A
Despres
Valérie
V
Vidal
Jean-Pierre
JP
Rossi
Jean-Claude
JC
Durand
Thierry
T
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
D003517:Cyclopentanes; D028441:F2-Isoprostanes; D005231:Fatty Acids, Unsaturated; D007202:Indicators and Reagents; C486066:phytoprostane F1