引用本文:
黄锦霞, 李焰, 周忠强, 周媛媛. 2-吡咯烷甲醇法合成切叶蚁警戒信息素[J]. 应用化学,
2000, 17(2): 206-208.
Citation: HUANG Jin-Xia, LI Yan, ZHOU Zhong-Qiang, ZHOU Yuan-Yuan. Synthesis of Alarm Pheromone of Leaf-Cutting Ant from 2-Hydroxymethyl Pyrrolidine[J]. Chinese Journal of Applied Chemistry, 2000, 17(2): 206-208.
Citation: HUANG Jin-Xia, LI Yan, ZHOU Zhong-Qiang, ZHOU Yuan-Yuan. Synthesis of Alarm Pheromone of Leaf-Cutting Ant from 2-Hydroxymethyl Pyrrolidine[J]. Chinese Journal of Applied Chemistry, 2000, 17(2): 206-208.
2-吡咯烷甲醇法合成切叶蚁警戒信息素
English
Synthesis of Alarm Pheromone of Leaf-Cutting Ant from 2-Hydroxymethyl Pyrrolidine
Abstract:
(S)-and (R)-2-hydrox ymethyl py rrolidine(2) were prepared from L-proline and D-glutamic acid, respectively. After acyla tion with propionic anhydride they gave 2-hydro-xymethyl-1-propionyl pyrrolidine(3). A chiral center was introduced into (3) on alkylation with propyl bromide in the presence of lithium diisopropy lamide(LDA) and (4) was formed. The alarm pheromone of leaf-cutting ant, (S) and (R)-4-methy l-3-heptanone (1) were obtained from (4) by acid hydroly sis and reacting with ethy llithium. Both isomers of (1) have optical yield of 85% e. e..
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Key words:
- methylhepta none
- / insect pheromone
- / pyrrolidine methanol
- / asymmetric alkylation
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