3,7-二甲基-2-十三碳醇乙酸酯的全合成

Total Synthesis of 3,7-Dimethyl-2-tridecanyl Acetate

对松叶蜂 ( Diprion pini)性信息素活性组分 3,7-二甲基 -2 -十三碳醇乙酸酯的全合成进行了研究 .提出了一条新的合成外消旋 3,7-二甲基 -2 -十三碳醇乙酸酯的合成路线 .以正辛醇为原料合成了 2 -甲基 -1 -辛烷基锂 ;以丙二酸二乙酯和 2 ,3-环氧丁烷为原料合成了 3,4 -二甲基 -γ-丁内酯 .2 -甲基 -1 -辛烷基锂与 3,4 -二甲基 -γ-丁内酯反应 ,得到的酮醇再经黄鸣龙还原 ,得到 3,7-二甲基 -2 -十三碳醇 ,酯化 ,得到 3,7-二甲基 -2 -十三碳醇乙酸酯 .

The total synthesis of 3,7-dimethyl-2-tridecanyl acetate, the active component of the sex pheromone of Diprion pini has been investigated. A new synthesis method of rac-3,7-dimethyl-2-tridecanyl acetate was proposed. 1-Bromo-2-methyl-octan-1-yl lithium was obtained from n-octanol for the first time, and 3,4-dimethyl-γ-butyrolactone was obtained from diethyl malonate and 2,3-epoxybutane. 2-Methyl-octan-1-yl lithium reacted with 3,4-dimethyl-γ-butyrolactone to give the ketoalcohol which via Huang-Minlong reaction afforded 3,7-dimethyl-2-tridecanol, and gave 3,7-dimethyl-2-tridecanyl acetate after acylation.