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

Guy, Alexandre; Oger, Camille; Heppekausen, Johannes; Signorini, Cinzia; De Felice, Claudio; Fürstner, Alois; Durand, Thierry; Galano, Jean-Marie

doi:10.1002/chem.201400380

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Oxygenated Metabolites of n-3 Polyunsaturated Fatty Acids as Potential Oxidative Stress Biomarkers: Total Synthesis of 8-F_3t-IsoP, 10-F_4t-NeuroP and [D4]-10-F_4t-NeuroP

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Heppekausen, Johannes
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Fürstner, Alois
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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引用

Guy, A., Oger, C., Heppekausen, J., Signorini, C., De Felice, C., Fürstner, A., Durand, T., & Galano, J.-M. (2014). Oxygenated Metabolites of n-3 Polyunsaturated Fatty Acids as Potential Oxidative Stress Biomarkers: Total Synthesis of 8-F_3t-IsoP, 10-F_4t-NeuroP and [D4]-10-F_4t-NeuroP. Chemistry - A European Journal, 20(21), 6374-6380. doi:10.1002/chem.201400380.

引用: https://hdl.handle.net/11858/00-001M-0000-0019-DA69-B

要旨

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-F_3t-IsoP and 10-F_4t-NeuroP as well as a deuterated derivative thereof were synthesized based on an acetylenic intermediate. An original approach achieved lateral chain insertion of 8-F_3t-IsoP by a ring-closing alkyne metathesis/semi-reduction strategy together with a temporary tether.