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Total synthesis of 4-F3t-neuroprostane and its 4-epimer |
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| Authors: | Anne-Laure Auvinet Alexandre Guy Thierry Durand |
| Institution: | a Institut des Biomolécules Max Mousseron, IBMM, UMR CNRS 5247, Université Montpellier 1, Université Montpellier 2, Faculté de Pharmacie, 15. Av. Ch. Flahault, F-34093 Montpellier Cedex 05, France b Department of Organic and Nuclear Chemistry and Centre for New Antivirals and Antineoplastics, Faculty of Science, Charles University, Hlavova 8, 128 43 Praha 2, Czech Republic c Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Flemingovo náměstí 2, 166 10 Praha 6, Czech Republic |
| Abstract: | The first synthesis of 4-F3t-Neuroprostane 1a and its 4-epimer is described. This molecule presents an important contribution to the study of neuronal oxidative stress in DHA-ω3 depleted brain. The key step involves the introduction of two unsaturated side chains into the chiral polyfunctional cyclopentane 4 via E selective HWE reaction and Z selective Wittig olefination for α and ω chains, respectively. |
| Keywords: | DPA Oxidative stress Neuroprostane Total synthesis Wittig HWE |
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