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Citation: MENG Yi, CHEN Li-Gong, XU Yan-Jie, GU Xian-Feng, SONG Yun. Total Synthesis of 3,7-Dimethyl-2-tridecanyl Acetate[J]. Chinese Journal of Applied Chemistry, ;2001, 18(12): 971-974. shu

Total Synthesis of 3,7-Dimethyl-2-tridecanyl Acetate

1.
School of Pharmaceuticals Science & Technology, Tianjin University, Tianjin 300072

Received Date: 10 May 2001
Available Online: 20 July 2001
Fund Project:

The total synthesis of 3,7-dimethyl-2-tridecanyl acetate, the active component of the sex pheromone of Diprion pini has been investigated. A new synthesis method of rac-3,7-dimethyl-2-tridecanyl acetate was proposed. 1-Bromo-2-methyl-octan-1-yl lithium was obtained from n-octanol for the first time, and 3,4-dimethyl-Ⅴ-butyrolactone was obtained from diethyl malonate and 2,3-epoxybutane. 2-Methyl-octan-1-yl lithium reacted with 3,4-dimethyl-Ⅴ-butyrolactone to give the ketoalcohol which via Huang-Minlong reaction afforded 3,7-dimethyl-2-tridecanol, and gave 3,7-dimethyl-2-tridecanyl acetate after acylation.
- pine sawfly,
- sex pheromone,
- dimethyl tridecanol,
- dimethyl tridecanyl acetate
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