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Oxygenated Metabolites of n‐3 Polyunsaturated Fatty Acids as Potential Oxidative Stress Biomarkers: Total Synthesis of 8‐F3t‐IsoP, 10‐F4t‐NeuroP and [D4]‐10‐F4t‐NeuroP |
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| Authors: | Dr Alexandre Guy Dr Camille Oger Dr Johannes Heppekausen Dr Cinzia Signorini Claudio De?Felice Prof Alois Fürstner Dr Thierry Durand Dr Jean‐Marie Galano |
| Institution: | 1. Institut des Biomolécules Max Mousseron,UMR 5247 ‐ CNRS ‐ University Montpellier I and II ‐ ENSCM, Faculty of Pharmacy, Montpellier (France), Fax: (+33)?411759553;2. Max‐Planck‐Institut für Kohlenforschung, 45470 Mülheim/Ruhr (Germany);3. Department of Molecular and Developmental Medicine, University of Siena, Siena (Italy);4. Neonatal Intensive Care Unit, University Hospital, Azienda Ospedaliera Universitaria Senese (AOUS), Siena (Italy) |
| Abstract: | A wide variety of metabolic products of polyunsaturated fatty acids is of paramount importance for improving our medical knowledge in the field of oxidized lipids. Two novel metabolites of n‐3 polyunsaturated fatty acids, 8‐F3t‐IsoP and 10‐F4t‐NeuroP as well as a deuterated derivative thereof were synthesized based on an acetylenic intermediate. An original approach achieved lateral chain insertion of 8‐F3t‐IsoP by a ring‐closing alkyne metathesis/semi‐reduction strategy together with a temporary tether. |
| Keywords: | fatty acids NeuroPs oxygenated metabolites ring‐closing metathesis total synthesis |