| 氮端Fmoc保护的Statine类化合物的合成 |
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| 引用本文： | 肖坤,王昕,沈竞康.氮端Fmoc保护的Statine类化合物的合成[J].合成化学,2006,14(4):375-377,394. |
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| 作者姓名： | 肖坤 王昕 沈竞康 |
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| 作者单位： | [1]中国科学院上海生命科学院上海药物研究所新药研究国家重点实验室,上海201203 [2]中国科学院研究生院,北京100049 |
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| 基金项目： | 高比容电子铝箔的研究开发与应用项目
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国家高技术研究发展计划(863计划)
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国家重点基础研究发展计划(973计划) |
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| 摘 要： | 采用DIC为羧基活化剂成功实现氮端Fmoc保护的亮氨酸与Meldrum's acid反应,生成1,3-二氧杂环己烷-4,6-二酮衍生物,后者无需纯化直接在乙酸乙酯中加热回流,自动关环产生Tetramic acid化合物.Tetramic acid用NaBH4还原得到4-羟基-吡咯烷酮类衍生物,继之水解,即得氮端Fmoc保护的Statine(6a).立体化学研究证明,6a具有3S,4S结构,且手性纯度很高.
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| 关 键 词： | Statine 活化剂 手性 合成 |
| 文章编号： | 1005-1511（2006）04-0375-03 |
| 收稿时间： | 2006-02-26 |
| 修稿时间： | 2006-02-26 |
Synthesis of N-Fmoc Statine and Its Analogue |
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| XIAO Kun, WANG Xin , SHEN Jing-kang.Synthesis of N-Fmoc Statine and Its Analogue[J].Chinese Journal of Synthetic Chemistry,2006,14(4):375-377,394. |
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| Authors: | XIAO Kun WANG Xin SHEN Jing-kang |
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| Institution: | 1. State Key Laboratory of Drug Research, Shanghai Institute of Materia Mediea, Shanghai Institutes for Biological Sciences, Chinese Academy of Sciences, Shanghai 201203, China; 2. Graduate School of the Chinese Academy of Sciences, Beijing 100049, China |
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| Abstract: | Employing DIC as carboxyl activating agent,N-Fmoc leucine reacted smoothly with Meldrum's acid to produce 1,3-dioxane-4,6-dione derivative,which was converted directly to tertramic acid by reflux with ethyl acetate without further purification.The resulting tetramic acid was reduced by NaBH_4 to afford 4-hydroxy-pyrrolidine-2-one derivative,which was further hydrolyzed in acid media to yield the desired N-Fmoc Statine.The chirality of the synthesized N-Fmoc Statine was also well studied. |
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| Keywords: | Statine activating agent chiral synthesis |
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