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谷蠹(Rhyzopertha dominica)是世界性储藏产物的主要害虫、在我国仓库中破坏性也占首位.1981年Williams等人首次鉴定和合成了这种信息素.它的两个活性组分是(E)-2-甲基-2-戊烯酸(S)-(+)-1-甲基丁基酯1和(E)-2,4-二甲基-2-戊烯酸(S)-(+)-1-甲基丁基酯2. Williams等人从自然界光学活性体——谷氨酸为原料,经过八步合成1或2,在合成过程中用了剧毒试剂氢化钠.本文报道的不对称合成主要应用Sharpless环氧化动力学拆分以及Wittig反应,以易得的巴豆醛为原料,经过四步得目的化合物,总得率30％,对映
Rhyzopertha dominica is a major pest of worldwide storage products and also has the highest destructiveness in our warehouses. This pheromone was first identified and synthesized by Williams et al in 1981. Its two active components are (E (S) - (+) - 1 -methylbutyl ester 1 and (E) -2,4-dimethyl- (+) - 1-methylbutyl ester 2. Williams et al. Used a highly toxic reagent, sodium hydride, in an eight-step synthesis of 1 or 2 starting from the optically active glutamate in nature. Reported the asymmetric synthesis of the main application of Sharpless epoxidation kinetic resolution and Wittig reaction, easy to get crotonaldehyde as the raw material, after four steps to obtain the desired compound, the total yield of 30%, Allergy