| 吉咪替康的合成新方法 |
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| 引用本文： | 肖锋,罗宇,吕伟,汤杰.吉咪替康的合成新方法[J].有机化学,2010,30(2):311-313. |
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| 作者姓名： | 肖锋 罗宇 吕伟 汤杰 |
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| 作者单位： | 华东师范大学化学系药物化学研究所,上海,200062 |
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| 基金项目： | 新世纪优秀人才支持计划 |
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| 摘 要： | 10-羟基喜树碱首先在N,N-二甲基甲酰胺(DMF)中经N-溴代丁二酰亚胺(NBS)溴代得到9-溴-10-羟基喜树碱, 9-溴-10-羟基喜树碱和氯甲酸乙酯反应得到9-溴-10-羟基喜树碱-10,20-双乙氧基碳酸酯(6). 化合物6和烯丙基三正丁基锡通过Stille偶联反应9]得到关键中间体7, 最后水解化合物7得到目标化合物. 通过柱层析纯化得到纯度大于99.8%, 单杂小于0.1%的吉咪替康(HPLC). 所有中间体及目标产物经1H NMR, 13C NMR, LRMS, HRMS表征确证.
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| 关 键 词： | 喜树碱 吉咪替康 合成 Stille偶联反应 |
| 收稿时间： | 2009-03-31 |
| 修稿时间： | 2009-08-01 |
A Novel Synthesis of Chimmitecan |
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| Xiao Feng,Luo Yu,Lü Wei,Tang Jie.A Novel Synthesis of Chimmitecan[J].Chinese Journal of Organic Chemistry,2010,30(2):311-313. |
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| Authors: | Xiao Feng Luo Yu Lü Wei Tang Jie |
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| Institution: | (Institute of Medicinal Chemistry, Department of Chemistry, East China Normal University, Shanghai 200062) |
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| Abstract: | 10-Hydroxy-camptothecin (2) was treated with N-bromosuccinimide (NBS) in N,N-dimethylformamide (DMF) to give bromide 5. The protection of the hydroxyl groups of bromide 5 with ethyl chloroformate afforded 6, which was reacted with allyltri-n-butyltin via Stille coupling reaction to give the coupling product 7. Subsequently, compound 7 was hydrolyzed to give the target compound. Purification via column chromatography on silica gel gave chimmitecan with more than 99.8% purity and with single impurity less than 0.1%. Structures of all compounds were confirmed by 1H NMR, 13C NMR, LRMS and HRMS techniques. |
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| Keywords: | camptothecin chimmitecan synthesis Stille coupling reaction |
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