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有机化学
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有机化学 ›› 2007, Vol. 27 ›› Issue (07): 866-869. 上一篇    下一篇

研究论文

一个简捷、高效合成松叶蜂性信息素的方法

王子坤，田伟生*，潘鑫复   

  1. (a兰州大学化学化工学院 功能有机分子化学国家重点实验室 兰州 730000)
    (b中国科学院上海有机化学研究所 上海 200032)
  • 收稿日期:2007-01-12 修回日期:1900-01-01 发布日期:2007-06-30
  • 通讯作者: 田伟生*

A Concise Synthesis of the Sex Pheromones of Pine Sawflies

WANG Zi-Kun,TIAN Wei-Sheng*,PAN Xin-Fu   

  1. (a State Key Laboratory of Applied Organic Chemistry, Department of Chemistry, Lanzhou University, Lanzhou 730000)
    (b Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032)
  • Received:2007-01-12 Revised:1900-01-01 Published:2007-06-30
  • Contact: TIAN Wei-Sheng*

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被引次数

4

以从甾体皂甙元降解的废弃物获取的(4R)-甲基-5-溴戊酸甲酯(4)为起始原料, 通过4与正庚基溴化镁选择性的偶联反应, 经关键合成中间体(4S)-甲基溴代十二烷(7)分别以52%和49%的总收率合成了松叶蜂性信息素(2S,3S,7S)-3,7-二甲基十五-2-醇乙酸酯(2)和丙酸酯(3).

关键词: 松叶蜂性信息素, (4R)-甲基-5-溴戊酸甲酯, 偶联反应

Starting from methyl (R)-5-bromo-4-methylpentanoate (4) obtained from the waste in the degradation of steroid sapogenin, (2S,3S,7S)-3,7-dimethylpentadecan-2-yl acetate (2) and propionate (3) were synthesized via the coupling reaction of 4 with heptyl Grignard in 52% and 49% overall yields respectively.

Key words: methyl (R)-5-bromo-4-methylpentanoate, coupling reaction, sex pheromone of Pine sawfly