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有机化学
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有机化学 ›› 2005, Vol. 25 ›› Issue (05): 558-560. 上一篇    下一篇

研究论文

松毛虫性信息素前体(4Z,6E)-十一碳二烯醛的合成

陶云海1,2，程伟贤1，黄相中1，张玉顺1，古昆*,a,b   

  1. (1云南大学化学与材料工程学院 昆明 650091)
    (2云南大学生物制药创新人才培养基地 昆明 650091)
  • 收稿日期:2004-05-07 修回日期:2004-11-23 发布日期:2004-04-30
  • 通讯作者: 古昆

Stereoselective Synthesis of (4Z,6E)-Dodecadien-1-al

TAO Yun-Hai1,2,CHENG Wei-Xian1,HUANG Xiang-Zhong1
ZHANG Yu-Shun1,GU Kun*,a,b   

  1. (Shool of Chemistry and Material, Yunnan University, Kunming 650091)
    (Center for Ad-vanced Studies of Medical and Organic Chemistry, Yunnan University, Kunming 650091)
  • Received:2004-05-07 Revised:2004-11-23 Published:2004-04-30
  • Contact: GU Kun

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从简单原料乙炔出发, 通过炔对丙烯醛的加成得到7-溴代-(4Z,6E)-庚二烯醛, 经乙二醇保护、Pd催化偶联、水解等步骤立体选择性地得到松毛虫性信息素前体(4Z,6E)-十一碳二烯醛.

关键词: (4Z,6E)-十一碳二烯醛, 立体选择性合成, 偶联反应

Starting from acetylene, 7-bromo-(4Z,6E)-heptadien-1-al was stereoselectively synthesized by the tandem addition reaction of acrolein with acetylene. Stereoselective synthesis of (4Z,6E)-dodecadien-1-al was achieved via three steps including palladium-catalyzed coupling reaction from 7-bromo-(4Z,6E)- heptadien-1-al.

Key words: stereoselective synthesis, coupling-reaction, (4Z,6E)-dodecadien-1-ol