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Citation: Huang Jinxia, Li Yan, Ma Xingquan, Chen Zuxing, Xu Zhanghuang. Synthesis of (2S,3R)-Sitophilate[J]. Chinese Journal of Applied Chemistry, ;1998, 15(2): 82-84. shu

Synthesis of (2S,3R)-Sitophilate

Department of Chemistry, Hubei University, Wuhan 430062

Received Date: 14 July 1997
Revised Date: 29 September 1997

(2S,3R)-Sitophilate, the major component of the aggregation pheromone of the granary weevil (Sitophilus granarius) was stereoselectively synthesized by a four-step sequence, using N-bornane-2,10-sultam as a chiral auxiliary. The key step was the asymmetric syn-aldolization of N-bropionyl bornane-2,10-sultam with propylaldehyde. The enantiometric excess of (2S,3R)-sitophilate was about 95% ee.
- (2S,3R)-sitophilate,
- synthesis,
- asymmetric syn-aldolization,
- N-bornane-sultam
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