全合成三尖杉碱的研究  

TOTAL SYNTHESIS OF (─) CEPHALOTAXINE

作　　者：钟三保[1] 刘维勤[1] 凌仰之[1] 李仁利[1] 涂光忠[1] 马立斌[1] 冯少良[1] 

机构地区：[1]北京医科大学药物化学教研室,北京微量化学研究所

出　　处：《中国药物化学杂志》1994年第2期84-88,共5页Chinese Journal of Medicinal Chemistry

基　　金：国家教委博士点基金

摘　　要：三尖杉碱是抗癌药物──三尖杉酯碱和高三尖杉酯碱的母体，在考察Ｗｅｉｎｒｅｂ路线的基础上，设计并完成了一条以胡椒醛和Ｌ－谷氨酸为起始原料，经１５步反应，合成三尖杉酮碱的路线，并用Ｌ－（＋）酒石酸拆分为三尖杉酮碱（─）旋光体和三尖杉酮碱（＋）旋光体。将拆分的三尖杉酮碱（─）旋光体用ＮａＢＨ４立体选择性还原为三尖杉碱（─），其光谱数据，理化参数，旋光性均与天然三尖杉碱一致。Cephalotaxine is the parent of harringtonine and homoharringtonine. Racemic cephalotaxine has been synthesized through sixteen steps from L-(+)glutamic and peperonal basesd on the Weinreb synthesis. Racemic cephalotaxinone was resoloved into a pair of enantiomers,(─)cephalotaxinone and (+)cephalotaxinone by using L-(+)tartaric acid as a resolving agent recrystallized from methanol. After stereoselective reduction of cephalotaxinone (─)with sodium boron hydride the goal compound,cephalotaxine(─)had the same configuration as natural cephalotaxine obtains and was verified by 1HNMR,13CNMR,MS,IR specta data,opticity and elementary analysis.

关 键 词：三尖杉碱 生物碱 拆分试剂 谷氨酸 胡椒醛 合成 

分 类 号：TQ464.4[化学工程—制药化工] R914.5[医药卫生—药物化学]