Asymmetric Synthesis of the Contact Sex Pheromone of Neoclytus acuminatus acuminatus (Fabricius)

doi:10.6023/cjoc202305023

Chinese Journal of Organic Chemistry ›› 2024, Vol. 44 ›› Issue (1): 301-308.DOI: 10.6023/cjoc202305023 Previous Articles Next Articles

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黑腹尼虎天牛接触性信息素的不对称合成

于士航, 刘嘉威, 安碧玉, 边庆花^*(), 王敏, 钟江春^*()

中国农业大学理学院应用化学系北京 100193

收稿日期:2023-05-17 修回日期:2023-06-24 发布日期:2023-07-19
作者简介:
^†共同第一作者.
基金资助:
国家重点研发计划(2017YFD0201404)

Asymmetric Synthesis of the Contact Sex Pheromone of Neoclytus acuminatus acuminatus (Fabricius)

Shihang Yu, Jiawei Liu, Biyu An, Qinghua Bian(), Min Wang, Jiangchun Zhong()

Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193

Received:2023-05-17 Revised:2023-06-24 Published:2023-07-19
Contact: *E-mail: zhong@cau.edu.cn; E-mail: bianqinghua@cau.edu.cn
About author:
^†These authors contributed equally to this work.
Supported by:
National Key Research and Development Program of China(2017YFD0201404)

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Abstract

Neoclytus acuminatus acuminatus (Fabricius) is a wood-boring pest of forests and orchards. Its contact sex pheromones were (R)-9-methylheptacosane, (R)-7-methylheptacosane and (R)-7-methylpentacosane. A new and efficient synthesis of the contact sex pheromone was developed from chiral synthon of (S)-2-methyloxirane. This procedure mainly involved ring-opening reaction of (S)-2-methyloxirane, S_N2 allylation of secondary tosylate and Wittig coupling of chiral aldehyde.

Key words: Neoclytus acuminatus acuminatus, contact sex pheromone, chiral source, (S)-2-methyloxirane, asymmetric synthesis

Cite this article

Shihang Yu, Jiawei Liu, Biyu An, Qinghua Bian, Min Wang, Jiangchun Zhong. Asymmetric Synthesis of the Contact Sex Pheromone of Neoclytus acuminatus acuminatus (Fabricius)[J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 301-308.

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Fig. & Tab. 6

Figure 1. Contact sex pheromone of Neoclytus acuminatus acuminatus

Scheme 1. Retrosynthetic analysis of contact sex pheromone 1

Scheme 2. Synthesis of chiral primary alcohol 10

Scheme 3. Synthesis of contact sex pheromone 1

Scheme 4. Synthesis of contact sex pheromones 2 and 3

Scheme 5. Synthesis of amides 23 and 24

References 28

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黑腹尼虎天牛接触性信息素的不对称合成

Asymmetric Synthesis of the Contact Sex Pheromone of Neoclytus acuminatus acuminatus (Fabricius)

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