(Z)-15-二十四碳烯酸的选择性合成

Selective synthesis of (Z)-15-tetracosenic acid

从易得原料芥酸(2)出发,通过酯化、还原、溴代反应得到溴代二十二碳烯(5),将5分别通过与乙酰乙酸乙酯和与丙二酸二乙酯反应生成中间体6和7,二者经成酸水解后脱羧均得到了具有药物活性的目标化合物(Z)-15-二十四碳烯酸,产物经甲酯化后通过GC-MS检测,其顺式结构比例大于90%.其结构经NMR,IR和MS表征.

（Z）-15-tetracosenic acid,a cis-configurated monounsaturated long-chain fatty acid which has various pharmaceutical activities,was synthesized from readily available raw material,erucic acid（2）.The synthesis was carried out through esterification,reduction and bromination to afford erucyl bromide 5,5 was then reacted with ethyl acetoacetate and diethyl malonate respectively to provide intermediates 6 and 7,both of them were hydrolyzed and decarboxylated to yield target compound 1 with cis-isomer content 90%.The structure of the product was characterized by NMR,IR and MS.