Total synthesis of (6R,12R)-6,12-dimethylpentadecan-2-one, the sex pheromone of Diabrotica balteata LeConte

IF 2.8 4区 化学 Q2 CHEMISTRY, ANALYTICAL Chirality Pub Date : 2024-02-27 DOI:10.1002/chir.23658
Jianwei Wu, Chuanwen Lin, Dan Liu, Qinghua Bian, Min Wang, Jiangchun Zhong
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Abstract

Diabrotica balteata LeConte is one of the most important polyphagous agricultural pests. The sex pheromone of this pest was synthesized using Evans asymmetric alkylation, ring-opening reaction of (R)-2-methyloxirane, SN2 alkylation of secondary tosylate, and coupling of chiral tosylate with Grignard reagent as central strategies. The sex pheromone prepared herein would be useful to control D. balteata.

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Diabrotica balteata LeConte 的性信息素 (6R,12R)-6,12-dimethylpentadecan-2-one 的全合成。
Diabrotica balteata LeConte 是最重要的多食性农业害虫之一。本研究以 Evans 不对称烷基化反应、(R)-2-甲基环氧乙烷的开环反应、仲对甲苯磺酸盐的 SN 2 烷基化反应以及手性对甲苯磺酸盐与格氏试剂的偶联反应为中心策略,合成了该害虫的性信息素。本文制备的性信息素将有助于控制 D. balteata。
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来源期刊
Chirality
Chirality 医学-分析化学
CiteScore
4.40
自引率
5.00%
发文量
124
审稿时长
1 months
期刊介绍: The main aim of the journal is to publish original contributions of scientific work on the role of chirality in chemistry and biochemistry in respect to biological, chemical, materials, pharmacological, spectroscopic and physical properties. Papers on the chemistry (physiochemical, preparative synthetic, and analytical), physics, pharmacology, clinical pharmacology, toxicology, and other biological aspects of chiral molecules will be published.
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