Stoffel W, Pruss H D
J Lipid Res. 1967 May;8(3):196-201.
A general procedure for the synthesis of 2-trans polyenoic fatty acids and of dl-3-hydroxypolyenoic acids is described. The 2-trans acids are prepared by LiAlH(4) reduction of a suitable polyenoic fatty acid ester to the alcohol, formation of the tosylate, oxidation to the aldehyde, and Doebner condensation of the latter with malonic acid. The 3-hydroxy acids are obtained by reaction of the acyl chloride of a suitable polyenoic acid with the sodium enolate of methyl acetoacetate and sodium methoxide to give the 3-keto ester, the keto group of which is reduced with sodium borohydride to the alcohol. These procedures were applied to the synthesis of eicosa-2-trans-8, 11, 14-all cis-tetraenoic acid-3-(14)C and DL-3-hydroxy eicosa-8, 11, 14-trienoic acid-3-(14)C.
本文描述了一种合成2-反式多烯脂肪酸和dl-3-羟基多烯脂肪酸的通用方法。通过用氢化铝锂将合适的多烯脂肪酸酯还原为醇，形成对甲苯磺酸酯，氧化为醛，然后使醛与丙二酸进行德布纳缩合反应来制备2-反式酸。通过使合适的多烯酸的酰氯与乙酰乙酸甲酯的烯醇钠和甲醇钠反应生成3-酮酯，然后用硼氢化钠将其酮基还原为醇来获得3-羟基酸。这些方法被应用于合成2-反式-8,11,14-全顺式-二十碳四烯酸-3-(14)C和DL-3-羟基-8,11,14-二十碳三烯酸-3-(14)C。
