高等学校化学学报

高等学校化学学报 ›› 2005, Vol. 26 ›› Issue (6): 1072.

• 研究论文 • 上一篇    下一篇

松毛虫性信息素(5Z,7E)-十二碳二烯醇的立体选择性合成

陶云海1,2, 程伟贤1, 张玉顺1, 古昆1,2   

  1. 1. 云南大学化学与材料工程学院;
    2. 云南大学生物制药创新人才培养基地, 昆明650091
  • 收稿日期:2004-06-12 出版日期:2005-06-10 发布日期:2005-06-10
  • 通讯作者: 古　昆(1945年出生),女,教授,从事有机合成研究.E-mail:gukun@ynu.edu.cn E-mail:gukun@ynu.edu.cn
  • 基金资助:

    云南省自然科学基金(批准号:2000B006M)资助.

Stereoselective Synthesis of(5Z,7E)-Dodecadien-1-ol

TAO Yun-Hai1,2, CHENG Wei-Xian1, ZHANG Yu-Shun1, GU Kun1,2   

  1. 1. School of Chemistry and Material Engineering;
    2. Biomedical Research and Training Center, Yunnan University, Kunming 650091, China
  • Received:2004-06-12 Online:2005-06-10 Published:2005-06-10

PDF (PC)

被引次数

8

摘要： 从简单原料乙炔出发,通过炔对丙烯醛的加成反应得到7-溴代-(4Z,6E)-庚二烯醛,再经乙二醇保护、Pd催化偶联、水解、Wittig反应和还原等步骤,立体选择性地得到松毛虫性信息素(5Z,7E)-十二碳二烯醇,其结构通过IR,NMR和MS等技术得到确认.

关键词: 松毛虫性信息素, (5Z, 7E)-十二碳二烯醇, 立体选择性合成, 偶联反应, 钯催化剂

Abstract: Sexpheromone of Dendrolimus Spp. is composed of (5Z, 7E)-5,7-Dodecadien-1-ol(1) and its acetate and propionate. At first 7-bromo-(4Z, 6E)-heptadien-1-al(2) was stereoselectively synthesized by the tandem addition reaction of acrolein with acetylene in the presence of Pd(OAc)2. Novel stereoselective synthesis of (5Z, 7E)-5,7-Dodecadien-1-ol was achieved in five steps, using palladium-catalyzed coupling reaction of 7-bromo-(4Z, 6E)-4,6-heptadiene-1-al ethylene acetal from production of the above aldehyde with Grignard reagent as the key step. The structures of all the compounds were confirmed by IR, NMR and MS spectra.

Key words: Dendrolimus Spp, (5Z,7E)-Dodecadien-1-ol, Stereoselective synthesis, Coupling-reaction, Palladium catalyst

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