Russ. J. Bioorganic Chem., 1996, 22(8):536-540

Synthesis of ketodienoic compounds from natural unsaturated fatty acids. 1. Linoleic acid

A preparative four-step procedure for converting the natural unsaturated fatty acids with the 1Z,4Z-pentadienoic fragment in 1-oxo-2E,4Z-dienoic compounds is described using linoleic acid methyl ester as an example. Natural linoleic acid methyl ester was oxidized with m-chloroperbenzoic acid in ethanol to a mixture of epoxides, methyl esters of coronaric and vernolic acids. Their subsequent treatment with anhydrous HBr in methanol yielded the mixture of bromohydrins oxidized by the Jones reagent to a mixture of bromoketones, which then were dehydrobrominated by 1,8-diazabicyclo[5.4.0]undecene-7. The separation of the resulting products by HPLC gave the methyl esters of (10E,12Z)-9-oxooctadecadienoic and (9Z,11E)-13-oxooctadecadienoic acids with a total yield of 30% at each of the four stages. The structures of the compounds synthesized were confirmed by UV, IR, and1H and13C NMR. © 1996 MAEe cyrillic signK Hayκa/Interperiodica Publishing.

Kuklev DV, Christie WW, Durand T, Rossi JC, Girard JP, Kasyanov SP, Akulin VN, Bezuglov VV

IBCH: 6313
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