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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. shu

Synthesis of Alarm Pheromone of Leaf-Cutting Ant from 2-Hydroxymethyl Pyrrolidine

1.
a Faculty of Chemistry and Material Science, Hubei University, Wuhan 430062;
2.
b Faculty of Life Science, Huazhong University of Science and Technology, Wuhan

Received Date: 25 August 1999
Available Online: 27 December 1999
Fund Project: 国家自然科学基金资助课题(29872012) (29872012)

(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..
- methylhepta none,
- insect pheromone,
- pyrrolidine methanol,
- asymmetric alkylation
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