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›› 2004, Vol. 24 ›› Issue (S1): 85-89.

• 研究报告 • Previous Articles     Next Articles

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

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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