| 脱氧三尖杉酯碱和高三尖杉酯碱的立体专一性合成 |
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| 引用本文： | 程家宠,张建华,张千兵,杨晶,黄量.脱氧三尖杉酯碱和高三尖杉酯碱的立体专一性合成[J].药学学报,1984,19(3):178-183. |
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| 作者姓名： | 程家宠 张建华 张千兵 杨晶 黄量 |
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| 作者单位： | 中国医学科学院药物研究所 北京
(程家宠，张建华，张千兵，杨晶)，中国医学科学院药物研究所 北京(黄量) |
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| 摘 要： | 本文报道脱氧三尖杉酯碱(Ⅵa)和高三尖杉酯碱(Ⅵc)的不对称合成。采用(+)R-对甲苯亚磺酰基乙酸叔丁酯(Ⅰ)与相应的三尖杉碱酮酸酯(Ⅱa)、(Ⅱb)进行立体选择性缩合反应,经过若干步骤,合成了具有C2′R构型的(Ⅵa)和(Ⅵc)。中间产物(Ⅲa),(Ⅲb)或(Ⅲc)以铝汞齐脱硫得(Ⅳa、(Ⅳc)。再以三氟醋酸处理,选择性水解叔丁酯得(Ⅴa)、(Ⅴc)。最后以重氮甲烷甲酯化。再次证实了(+)R-对甲苯亚磺酰基乙酸叔丁酯(Ⅰ)具有较高的立体选择性反应。
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| 关 键 词： | (+)R-对甲苯亚磺酰基乙酸叔丁酯 三尖杉碱酮酸酯 立体专一性合成 脱氧三尖杉酯碱 高三尖杉酯碱 |
| 收稿时间： | 1982-10-11 |
STEREOSPECIFIC SYNTHESIS OF DEOXYHARRINGTONINE AND HOMOHARRINGTONINE |
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| CHENG Jia-chong,ZHANG Jian-hua,ZHANG Qian-bing,YANG Jing and HUANG Liang.STEREOSPECIFIC SYNTHESIS OF DEOXYHARRINGTONINE AND HOMOHARRINGTONINE[J].Acta Pharmaceutica Sinica,1984,19(3):178-183. |
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| Authors: | CHENG Jia-chong ZHANG Jian-hua ZHANG Qian-bing YANG Jing and HUANG Liang |
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| Abstract: | The asymmetric synthesis of deoxyharringtonine and homoharringtonine has been described.The stereospecific condensation of chiral a-sulfinylester (Ⅰ) and corresponding a-keto-acyl-cephalotaxine (Ⅱa) and (Ⅱb) was used to introduce the asymmetric C2' with the desired configuration. The condensation products (Ⅲa) and (Ⅲc) wero desulfurized with aluminum amalgam to give compounds (Ⅳa) and (Ⅳc) which were hydrolyzed with trifluoroacetic acid to remove t-butyl group. The final products were obtained by methylation with diazomethane.The higher steric selectivity in the reaction of chiral (+)Ra-sulfinylester (Ⅰ) was again demonstrated. |
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| Keywords: | α-Keto-acyl-cephalotaxine Stereospecific synthesis Deoxyharringtonine Homoharringtonine Chiral α-sulfinylester |
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