167820-65-7Relevant articles and documents
Direct preparation of (Z,Z)-1,4-dienic units with a new C6 homologating agent: Synthesis of α-linolenic acid
Sandri,Viala
, p. 271 - 275 (1995)
Syntheses of two C6 homologating agents 2a and 2f are described. These agents allow direct access to the (Z,Z)-1,4-diene unit 3, a moiety present in a wide number of natural compounds. Compound 2a is prepared in 40% overall yield by selective epoxidation of methoxycyclohexa-1,4-diene followed by oxidative ring cleavage and transatalization. Compound 2f is obtained in 90% yield by a one-step oxidative dimerization of phosphonium salt 1. A short synthetic application of these two new C6 homologating agents to the synthesis of α-linolenic acid is described.
Total syntheses and in vivo quantitation of novel neurofuran and dihomo-isofuran derived from docosahexaenoic acid and adrenic acid
De La Torre, Aurlien,Lee, Yiu Yiu,Mazzoni, Attilio,Guy, Alexandre,Bultel-Ponc, Valrie,Durand, Thierry,Oger, Camille,Lee, Jetty Chung-Yung,Galano, Jean-Marie
supporting information, p. 2442 - 2446 (2015/01/30)
Neurofurans (NeuroFs) and dihomo-isofurans (dihomo-IsoFs) are produced in vivo by non-enzymatic free-radical pathways from docosahexaenoic and adrenic acids, respectively. As these metabolites are produced in minute amounts, their analyses in biological samples remain challenging. Syntheses of neurofuran and dihomo-isofurans described are based on a pivotal strategy, thanks to an enantiomerically enriched intermediate, which allowed, for the first time, access to both families: the alkenyl and enediol. Owing to this formation, quantitation of specific NeuroF and dihomo-IsoFs in biological samples was attainable.
Total synthesis and bioactivities of two proposed structures of maresin
Sasaki, Kenji,Urabe, Daisuke,Arai, Hiroyuki,Arita, Makoto,Inoue, Masayuki
experimental part, p. 534 - 543 (2011/10/12)
Maresin is a potent anti-inflammatory lipid mediator derived from docosahexaenoic acid (DHA). A highly convergent total synthesis of two proposed structures of C7-epimeric maresins from the four known fragments was achieved in 17 steps. The three key coupling reactions were the BF3-mediated alkyne attack on the epoxide, chiral titanium complex-promoted enantioselective alkyne addition to the aldehyde, and a Julia-Kocienski olefination. The two synthesized diastereomers were found to be comparably active in blocking neutrophil infiltration in the acute peritonitis model. Copyright