Enantioselective Synthesis of the Sex Pheromone of Sitodiplosis mosellana (Géhin) and Its Stereoisomers

(2<i>S</i>,7<i>S</i>)-2,7-Nonanediyl dibutyrate is the sex pheromone of <i>Sitodiplosis mosellana</i> (Géhin). In this study, this sex pheromone and its three stereoisomers were prepared. Central to this strategy was the ring opening of chiral epoxide with an alkynyllithium and the hydrogenation of the triple bond. Moreover, this approach consisted of six steps, and the total yields were 59-64%.

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Publication Details

Journal
Molecules
Published
2025-02-03
DOI
https://doi.org/10.3390/molecules30030671
Primary Topic
Synthetic Organic Chemistry Methods
Type
article
Field-Weighted Citation Impact
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article

Enantioselective Synthesis of the Sex Pheromone of Sitodiplosis mosellana (Géhin) and Its Stereoisomers

Qinghua Bian, Jiangchun Zhong, Yun Zhou, Jianan Wang et al.
Molecules
Synthetic Organic Chemistry Methods
article

Enantioselective Synthesis of the Sex Pheromone of Sitodiplosis mosellana (Géhin) and Its Stereoisomers

Qinghua Bian, Jiangchun Zhong, Yun Zhou, Jianan Wang, Xiaoyang Li
article en

Abstract

(2<i>S</i>,7<i>S</i>)-2,7-Nonanediyl dibutyrate is the sex pheromone of <i>Sitodiplosis mosellana</i> (Géhin). In this study, this sex pheromone and its three stereoisomers were prepared. Central to this strategy was the ring opening of chiral epoxide with an alkynyllithium and the hydrogenation of the triple bond. Moreover, this approach consisted of six steps, and the total yields were 59-64%.

MoleculesVol. 30(3)
Shandong Academy of Agricultural Sciences (CN), China Agricultural University (CN)
Openalex Percentile: Top 98%
Synthetic Organic Chemistry Methods
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