| 雌舞毒蛾引诱剂: (＋)-(7R,8S)-7,8-环氧-2-甲基十八烷的不对称全合成 |
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| 引用本文： | 张朝欣,达世俊,张化冰,孙彬,李瀛.雌舞毒蛾引诱剂: (＋)-(7R,8S)-7,8-环氧-2-甲基十八烷的不对称全合成[J].化学学报,2007,65(21):2433-2436. |
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| 作者姓名： | 张朝欣 达世俊 张化冰 孙彬 李瀛 |
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| 作者单位： | 兰州大学功能有机分子化学国家重点实验室,兰州,730000 |
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| 摘 要： | 由雌舞毒蛾释放的性引诱剂由于在害虫防治方面的需求不断增加, 已有许多文献对其合成方法进行报道. 以正十一醛和环戊酮为起始原料, 用L-脯氨酸催化的不对称羟醛缩合反应构筑手性中心, 后经拜耶-维利格氧化, 维梯希烯化等步骤, 为雌舞毒蛾性引诱剂(＋)-(7R,8S)-7,8-环氧-2-甲基十八烷提供了一条简便高效的不对称合成新途径, 总收率为37.8%.
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| 关 键 词： | 舞毒蛾性信息素 L-脯氨酸催化的羟醛缩合反应 拜耶-维利格反应 维梯希反应 |
| 收稿时间： | 2006-12-8 |
| 修稿时间： | 2006-12-08 |
Asymmetric Total Synthesis of (+)-Disparlure: (+)-(7R,8S)-cis-7,8-epoxy-2-methyloctadecane |
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| ZHANG Chao-Xin,DA Shi-Jun,ZHANG Hua-Bing,SUN Bin,LI Ying.Asymmetric Total Synthesis of (+)-Disparlure: (+)-(7R,8S)-cis-7,8-epoxy-2-methyloctadecane[J].Acta Chimica Sinica,2007,65(21):2433-2436. |
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| Authors: | ZHANG Chao-Xin DA Shi-Jun ZHANG Hua-Bing SUN Bin LI Ying |
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| Institution: | State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000 |
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| Abstract: | (＋)-Disparlure is the sex attractant emitted by the female gypsy moth. Because of the growing demand for pest control, many syntheses of (＋)-disparlure have been reported. The concise and efficient asymmetric total synthesis of (＋)-disparlure was accomplished, starting from undecanal and cyclopentanone by using L-proline-catalyzed asymmetric aldol reaction to construct the chiral lactone, then by Baeyer-Vil-liger oxidation and Wittig olefination, providing a new strategy on the synthesis of (＋)-(7R,8S)-cis-7,8-epoxy-2-methyloctadecane in a total yield of 37.8%. |
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| Keywords: | (＋)-disparlure L-proline-catalyzed aldol reaction Baeyer-Villiger oxidation Wittig olefination |
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