Simple Synthesis of (Z)-7-Eicosen-11-one- the Sex Pheromone of Peach Fruit Moth

doi:10.6023/cjoc201401021

Chin. J. Org. Chem. ›› 2014, Vol. 34 ›› Issue (7): 1458-1461.DOI: 10.6023/cjoc201401021 Previous Articles Next Articles

Notes

桃小食心虫性信息素——（Z）-7-二十碳烯-11-酮的简便合成

杨晓梅^a, 张玉顺^b, 姚赟^b, 陶云海^b

a 云南中医学院中药学院昆明 650500;
b 云南大学化学科学与工程学院昆明 650091

收稿日期:2014-01-13 修回日期:2014-03-16 发布日期:2014-04-01
通讯作者: 陶云海 E-mail:cloudsea2000@163.com
基金资助:
云南大学理（工）科校级科研（No.2011YB12）及云南省教育厅基金（No.2011Y112）资助项目.

Simple Synthesis of (Z)-7-Eicosen-11-one- the Sex Pheromone of Peach Fruit Moth

Yang Xiaomei^a, Zhang Yushun^b, Yao Yun^b, Tao Yunhai^b

a School of Traditional Chinese Medicine, Yunnan University of Traditional Chinese Medicine, Kunming 650500;
b School of Chemistry Science and Engineering, Yunnan University, Kunming 650091

Received:2014-01-13 Revised:2014-03-16 Published:2014-04-01
Supported by:
Project supported by the Science and Technology Foundation of Yunnan University (No. 2011YB12) and the Foundation of Yunnan Province Department of Education (No. 2011Y112).

Peach fruit moth is one of the most serious pests, whose sex pheromone is (Z)-7-eicosen-11-one. Synthesis of the compound was achieved from 2,3-dihydrofuran. Firstly, acidic hydrolysis of 2,3-dihydrofuran gave 4-hydroxybutanal, which reacted with the ylide prepared from heptyltriphenylphosphonium bromide to afford (Z)-4-undecen-1-ol. The alcohol was oxidated followed by Grignard addition and further oxidation to give the target product.

Key words: carposina sasakii matsumura, (Z)-7-eicosen-11-one, pheromone synthesis, Wittig reaction, Grignard addition

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Yang Xiaomei, Zhang Yushun, Yao Yun, Tao Yunhai. Simple Synthesis of (Z)-7-Eicosen-11-one- the Sex Pheromone of Peach Fruit Moth[J]. Chin. J. Org. Chem., 2014, 34(7): 1458-1461.

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桃小食心虫性信息素——（Z）-7-二十碳烯-11-酮的简便合成

Simple Synthesis of (Z)-7-Eicosen-11-one- the Sex Pheromone of Peach Fruit Moth

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