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高等学校化学研究 ›› 1999, Vol. 15 ›› Issue (3): 238-242.

• Articles • 上一篇    下一篇

Stereoselective Synthesis of the Pheromones of Ant Tetramorium Impurm and Leptogenys Diminuta

LI Yan, HUANG Jin-xia, ZHOU Zhong-qiang, CHEN Zu-xing, XU Zhang-huang   

  1. Faculty of Chemistry and Material Science, Hubei University, Wuhan 430062, P. R. China
  • 收稿日期:1999-01-19 出版日期:1999-08-24 发布日期:2011-08-17
  • 通讯作者: LI Yan
  • 基金资助:

    Supported by the National Natural Science Foundation of China.

Stereoselective Synthesis of the Pheromones of Ant Tetramorium Impurm and Leptogenys Diminuta

LI Yan, HUANG Jin-xia, ZHOU Zhong-qiang, CHEN Zu-xing, XU Zhang-huang   

  1. Faculty of Chemistry and Material Science, Hubei University, Wuhan 430062, P. R. China
  • Received:1999-01-19 Online:1999-08-24 Published:2011-08-17
  • Supported by:

    Supported by the National Natural Science Foundation of China.

PDF (PC)

摘要： (R,4S)-4-Methyl-3-hexanol and ( 3R,4S )-4-methyl-3-heptanol, which are the pheromones of ant Tetramorium impurm and Leptogenys diminuta, were stereoselectively synthesized by six-step sequence starting from N-bornane-10,2-sultam separately, the two asymmetric carbon atoms of the target products were created by employing asymmetric syn aldolization of N-acylbornane-10,2-sultam with propylaldehyde. The enantiomeric excess of the target products prepared by this route is over 92%.

关键词: Pheromone, Asymmetric syn-aldolization, N-Bornane-10, 2-sultam

Abstract: (R,4S)-4-Methyl-3-hexanol and ( 3R,4S )-4-methyl-3-heptanol, which are the pheromones of ant Tetramorium impurm and Leptogenys diminuta, were stereoselectively synthesized by six-step sequence starting from N-bornane-10,2-sultam separately, the two asymmetric carbon atoms of the target products were created by employing asymmetric syn aldolization of N-acylbornane-10,2-sultam with propylaldehyde. The enantiomeric excess of the target products prepared by this route is over 92%.

Key words: Pheromone, Asymmetric syn-aldolization, N-Bornane-10,2-sultam