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

ABSTRACT: 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.

SUBMITTER: Wang X

PROVIDER: S-EPMC9611917 | biostudies-literature | 2022 Oct

REPOSITORIES: biostudies-literature

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

Wang Xueyang X Wang Jianan J Ma Fengbo F Bian Qinghua Q Wang Min M Zhong Jiangchun J

Molecules (Basel, Switzerland) 20221014 20

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. ...[more]

PMID: 36296492

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