Asymmetric Synthesis of Contact Sex Pheromone of <i>Tetropium fuscum</i> and Its Enantiomer
<i>Tetropium fuscum</i> is a harmful forest pest and attacks spruces. The contact sex pheromone of this pest, (<i>S</i>)-11-methyl-heptacosane, and its enantiomer were synthesized via Evans’ chiral auxiliaries. The key steps of this approach included acylation of carboxylic a...
| Main Authors: | , , , , , |
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| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2022-10-01
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| Series: | Molecules |
| Subjects: | |
| Online Access: | https://www.mdpi.com/1420-3049/27/20/6897 |
| Summary: | <i>Tetropium fuscum</i> is a harmful forest pest and attacks spruces. The contact sex pheromone of this pest, (<i>S</i>)-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. |
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| ISSN: | 1420-3049 |