Asymmetric Synthesis of Contact Sex Pheromone of Tetropium fuscum and Its Enantiomer

Tetropium fuscum is a harmful forest pest and attacks spruces. The contact sex pheromone of this pest, (S)-11-methyl-heptacosane, and its enantiomer were synthesized via Evans’ chiral auxiliaries. The key steps of this approach included acylation of carboxylic acid, diastereoselective methylation of...

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Veröffentlicht in:Molecules (Basel, Switzerland) Switzerland), 2022-10, Vol.27 (20), p.6897
Hauptverfasser: Wang, Xueyang, Wang, Jianan, Ma, Fengbo, Bian, Qinghua, Wang, Min, Zhong, Jiangchun
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Sprache:eng
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Zusammenfassung:Tetropium fuscum is a harmful forest pest and attacks spruces. The contact sex pheromone of this pest, (S)-11-methyl-heptacosane, and its enantiomer were synthesized via Evans’ chiral auxiliaries. The key steps of this approach included acylation of carboxylic acid, diastereoselective methylation of oxazolidinone amide, and Wittig coupling of the aldehyde with chiral phosphonium salt. The synthetic pheromones would have potential utility in the control of this pest.
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules27206897