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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 [D 4 ]‐10‐F 4t ‐NeuroP
Author(s) -
Guy Alexandre,
Oger Camille,
Heppekausen Johannes,
Signorini Cinzia,
De Felice Claudio,
Fürstner Alois,
Durand Thierry,
Galano JeanMarie
Publication year - 2014
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201400380
Subject(s) - polyunsaturated fatty acid , chemistry , ring closing metathesis , metathesis , derivative (finance) , stereochemistry , fatty acid , biochemistry , organic chemistry , polymerization , polymer , financial economics , economics
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.