Acta Chimica Sinica ›› 2007, Vol. 65 ›› Issue (21): 2433-2436. Previous Articles     Next Articles

雌舞毒蛾引诱剂: (+)-(7R,8S)-7,8-环氧-2-甲基十八烷的不对称全合成


  1. (兰州大学功能有机分子化学国家重点实验室 兰州 730000)
  • 投稿日期:2006-12-08 修回日期:2007-04-17 发布日期:2007-11-14
  • 通讯作者: 李瀛

Asymmetric Total Synthesis of (+)-Disparlure: (+)-(7R,8S)-cis-7,8- ep-oxy-2-methyloctadecane

ZHANG Chao-Xin; DA Shi-Jun; ZHANG Hua-Bing; SUN Bin; LI Ying   

  1. (State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000)
  • Received:2006-12-08 Revised:2007-04-17 Published:2007-11-14
  • Contact: LI Ying

(+)-Disparlure is the sex attractant emitted by the female gypsy moth. Because of the growing demand for pest control, many syntheses of (+)-disparlure have been reported. The concise and efficient asymmetric total synthesis of (+)-disparlure was accomplished, starting from undecanal and cyclopentanone by using L-proline-catalyzed asymmetric aldol reaction to construct the chiral lactone, then by Baeyer-Vil-liger oxidation and Wittig olefination, providing a new strategy on the synthesis of (+)-(7R,8S)-cis-7,8-epoxy-2-methyloctadecane in a total yield of 37.8%.

Key words: (+)-disparlure, L-proline-catalyzed aldol reaction, Baeyer-Villiger oxidation, Wittig olefination