Asymmetric synthesis of (R)-2,6-dimethylhept-5-en-1-ol, sex pheromone of acarid mites, Tyreophagus sp. (Astigmata: Acaridae)
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摘要: 粉螨Tyreophagus sp. 包括许多危害农作物的重要害虫和仓储害虫，而(R)-2,6-二甲基-5-庚烯-1-醇为粉螨 性信息素的主要成分。本研究首次利用Evans手性助剂法构建该性信息素的手性叔碳中心，以戊醛酸甲酯为原料，经过Wittig偶联、LiOH水解、甲基化及硼氢化钠还原等6步反应，完成了该信息素的不对称合成。Abstract: Many acrid mites are significant pests that damage crops and grain warehouses, and (R)-2,6-dimethylhept-5-en-1-ol is the main component of the sex pheromone of the acrid mite Tyreophagus sp. Here, the chiral tertiary carbon center of this sex pheromone was constructed by Evans chiral auxiliary method for the first time, and the asymmetric synthesis of this pheromone was completed by a six-step reaction of Wittig coupling, LiOH hydrolysis, methylation, and NaBH4 reduction using methyl glutarate as the raw material.
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Key words:
- acarid mite /
- sex pheromone /
- symmetric synthesis /
- chiral auxiliary
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