Asymmetric Synthesis of Three Alkenyl Epoxides: Crafting the Sex Pheromones of the Elm Spanworm and the Painted Apple Moth

A concise synthesis of the sex pheromones of elm spanworm as well as painted apple moth has been achieved. The key steps were the alkylation of acetylide ion, Sharpless asymmetric epoxidation and Brown's P2-Ni reduction. This approach provided the sex pheromone of the elm spanworm ( ) in 31% to...

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Published inMolecules (Basel, Switzerland) Vol. 29; no. 9; p. 2136
Main Authors Zhou, Yun, Wang, Jianan, Tian, Beijing, Zhu, Yanwei, Zhang, Yujuan, Han, Jinlong, Zhong, Jiangchun, Shan, Chenggang
Format Journal Article
LanguageEnglish
Published Switzerland MDPI AG 01.05.2024
Subjects
Agricultural production
Alcohol
alkenyl epoxides
Animals
asymmetric synthesis
Chromatography
Cockroaches
elm spanworm
Epoxy Compounds - chemistry
Molecular Structure
Moths
Organic compounds
painted apple moth
Pheromones
Sex Attractants - chemical synthesis
Sex Attractants - chemistry
sex pheromone
Synthesis
China
Beijing China
alkenyl epoxides
asymmetric synthesis
sex pheromone
elm spanworm
painted apple moth
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Summary:A concise synthesis of the sex pheromones of elm spanworm as well as painted apple moth has been achieved. The key steps were the alkylation of acetylide ion, Sharpless asymmetric epoxidation and Brown's P2-Ni reduction. This approach provided the sex pheromone of the elm spanworm ( ) in 31% total yield and those of the painted apple moth ( , ) in 26% and 32% total yields. The ee values of three final products were up to 99%. The synthesized pheromones hold promising potential for use in the management and control of these pests.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:1420-3049
1420-3049
DOI:10.3390/molecules29092136