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化学学报
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化学学报 ›› 2007, Vol. 65 ›› Issue (21): 2433-2436. 上一篇    下一篇

研究论文

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

张朝欣，达世俊，张化冰，孙彬，李瀛   

  1. (兰州大学功能有机分子化学国家重点实验室 兰州 730000)
  • 投稿日期:2006-12-08 修回日期:2007-04-17 发布日期:2007-11-14
  • 通讯作者: 李瀛

Asymmetric Total Synthesis of (＋)-Disparlure: (＋)-(7R,8S)-cis-7,8- ep-oxy-2-methyloctadecane

ZHANG Chao-Xin; DA Shi-Jun; ZHANG Hua-Bing; SUN Bin; LI Ying   

  1. (State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000)
  • Received:2006-12-08 Revised:2007-04-17 Published:2007-11-14
  • Contact: LI Ying

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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%.

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

(＋)-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%.

Key words: (＋)-disparlure, L-proline-catalyzed aldol reaction, Baeyer-Villiger oxidation, Wittig olefination