| 合成天然产物曲古抑菌素A的新方法 |
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| 引用本文： | 赵曦,张士磊,段文虎.合成天然产物曲古抑菌素A的新方法[J].有机化学,2007,27(12):1509-1515. |
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| 作者姓名： | 赵曦 张士磊 段文虎 |
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| 作者单位： | 1. 中国科学院上海生命科学研究院上海药物研究所,上海,201203
2. 中国科学院上海生命科学研究院上海药物研究所,上海,201203;华东理工大学药学院药物科学系,上海,200237 |
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| 基金项目： | 中国科学院知识创新工程重要方向(No.06G8031014)，国家863(No.2006AA020602)资助项目. |
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| 摘 要： | 报道了一条组蛋白去乙酰化酶抑制剂曲古抑菌素A的有效合成路线. 通过L-脯氨酸催化对硝基苯甲醛与丙醛的羟醛缩合反应, 高立体选择性地构建了目标分子的手性中心, 羟醛缩合产物的ee值大于99%, anti∶syn＝16∶1. 随后的合成过程中无消旋化现象, 合成的曲古抑菌素A是单一R型异构体, ee值大于99%.
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| 关 键 词： | 曲古抑菌素A 组蛋白去乙酰酶抑制剂 L-脯氨酸 合成 |
| 收稿时间： | 2007-03-30 |
| 修稿时间： | 2007-06-06 |
A New Synthetic Method of Natural Product Trichostatin A |
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| ZHAO,Xi,ZHANG,Shi-Lei,DUAN,Wen-Hu.A New Synthetic Method of Natural Product Trichostatin A[J].Chinese Journal of Organic Chemistry,2007,27(12):1509-1515. |
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| Authors: | ZHAO Xi ZHANG Shi-Lei DUAN Wen-Hu |
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| Institution: | (Department of Medicinal Chemistry, Shanghai Institute of Materia Medica, Shanghai Institutes for Biological Sciences, Chinese Academy of Sciences, Shanghai 201203)(Department of Pharmaceutical Sciences, School of Pharmacy, East China University of Science & Technology, Shanghai 200237) |
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| Abstract: | An efficient synthesis of trichostatin A, a potent histone deacetylase inhibitor, was reported. The key point in this new approach lied in the highly stereocontrolled establishment of its chiral center using L-proline-catalyzed aldol reaction between p-nitrobenzaldehyde and propaldehyde. The aldol product was obtained with ＞99% ee and high de (anti∶syn＝16∶1). No racemization was found in the following process and the synthetic trichostatin A was a pure R enantiomer with more than 99% ee. |
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| Keywords: | trichostatin A histone deacetylase inhibitor L-proline synthesis |
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