| 经由胂叶立德立体有择合成仿保幼激素──增丝素（ZR－512）及其（2Z，4E）－异构体 |
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| 引用本文： | 刘天麟,倪赤友,谢文权,李正名.经由胂叶立德立体有择合成仿保幼激素──增丝素（ZR－512）及其（2Z，4E）－异构体[J].高等学校化学学报,1994(3). |
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| 作者姓名： | 刘天麟 倪赤友 谢文权 李正名 |
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| 作者单位： | 南开大学元素有机化学研究所 |
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| 摘 要： | ３－甲基－２－丁烯酸乙酯４经ＳｅＯ２反式氧化、还原、溴化得到关键中间体４－溴－３－甲基－（２Ｅ）－丁烯酸乙酯７．７与三苯基胂反应生成季８．二氢香茅醛与８在Ｋ＿２ＣＯ＿３－乙醇－微量水的存在下反应，得到（２Ｅ，４Ｅ）－３，７，１１－三甲基－２，４－十二碳二烯酸乙酯１ａ及其（２Ｚ，４Ｅ）－异构体１ｂ，产率７４％。该反应具有（４Ｅ）－立体选择性，同时Ｃ－２双键发生部分构型转化。
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| 关 键 词： | 增丝素（ZR－512），胂叶立德，立体选择性，合成 |
Stereoselective Synthesis of Hydroprene and Its(2Z, 4E)-Isomer via Arsonic Ylide |
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| LIU Tian-Lin, NI Chi-You, XIE Wen-Quan, LI Zheng-Ming.Stereoselective Synthesis of Hydroprene and Its(2Z, 4E)-Isomer via Arsonic Ylide[J].Chemical Research In Chinese Universities,1994(3). |
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| Authors: | LIU Tian-Lin NI Chi-You XIE Wen-Quan LI Zheng-Ming |
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| Abstract: | The key intermediate ethyl 4-bromo-3-methyl-( 2E)-butenoate 7 was obtained from ethyl 3-methyl-2-butenoate 4 by a sequence of reactions:trans-oxidation(SeO2), reduction and bromination, Reaction of 7 and triphenylarsine gave the arsonium salt 8.Finally, reaction of 8 and dihydrocitronellal in the presence of K_2CO_3-C_2H_5OH-trace H_2O afforded hydroprene and its (2Z, 4E)-isomer in yield of 74%. The(4E)-selectivity and the partial inversion of C-2 double bond configuration happened in this reaction. |
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| Keywords: | Hydroprene Arsonic Ylide Stereoselectivity Synthesis |
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