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林产化学与工业

林产化学与工业 ›› 2004, Vol. 24 ›› Issue (S1): 85-89.

• 研究报告 • 上一篇    下一篇

由香茅醛到保幼激素类似物ZR-515的简便全合成

朱新海1, 江焕峰1, 田兴山2, 冉学光1   

  1. 1. 中国科学院 广州化学研究所, 广东 广州 510650;2. 广东省农科院 生物技术研究所, 广东 广州 510640
  • 收稿日期:2003-10-27 修回日期:1900-01-01 出版日期:2004-10-20 发布日期:2004-10-20

A FACILE ROUTE FOR TOTAL SYNTHESIS OF THE JUVENILE HORMONE ANALOGUE ZR-515 FROM CITRONELLAL

ZHU Xin-hai1, JIANG Huan-feng1, TIAN Xing-shan2, RAN Xue-guang1   

  1. 1. Guangzhou Institute of Chemistry, Chinese Academy of Sciences, Guangzhou 510650, China;2. Bio -Tech Research Institute, Guangdong Academy of Agricultural Science, Guangzhou 510640, China
  • Received:2003-10-27 Revised:1900-01-01 Online:2004-10-20 Published:2004-10-20

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摘要： 以香茅醛为起始原料,首先与丙酮进行羟醛缩合反应,继而在金属锌的存在下与α-溴乙酸乙酯进行Reformatskii反应得到目标碳链,然后再经水解、酯化和醚化,最终成功地全合成了具有保幼激素活性的昆虫生长调节剂ZR-515及其异构体,即11-甲氧基-3,7,11-三甲基-(2E,4E)-十二碳二烯酸异丙酯。其中具有较高生物活性的(2E,4E)-异构体(ZR-515)的含量达56%。各步所合成化合物的结构经IR、MS、1HNMR证实。

关键词: 保幼激素类似物, 11-甲氧基-3, 11-三甲基-(2E, 4E)-十二碳二烯酸异丙酯, 香茅醛

Abstract: Dimethylundeca-3,9-dien-2-one was prepared from the starting material citronellal reacting with acetone via aldol condensation, followed by reacting with α-bromoethyl acetate in the presence of Zn through Reformatskii reaction to obtain target chain. After hydrolysis, esterification and etherification, the isomeric products, isopropy-11-methoxy-3,7,11-trimethy1-(2E,4E)-dodecadienoate, which possess juvenile hormone activity, were succeededly synthesized, in which the (2E,4E)-stereoisomer ZR-515, which showed considerably higher activity than other isomers, amounted to 56%. The structures of all compounds in each step were confirmed by 1H NMR、IR and MS.

Key words: juvenile hormone analogue, (2E, 4E)-isopropy-11-methoxy-3, 11-trimethyl-dodeca-dienoate, citronellal

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