Synthesis of corn rootworm pheromones from commercial diols |
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Authors: | Thanh-Danh Nguyen Cong-Hao Nguyen Chan Im Chi-Hien Dang |
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Institution: | 1.Department of Pharmaceutical Chemistry Technology, Institute of Chemical Technology,Vietnam Academy of Science and Technology,Ho Chi Minh City,Vietnam;2.Department of Chemistry,Konkuk University,Seoul,Republic of Korea |
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Abstract: | A mixture of stereoisomers of the corn rootworm pheromones was synthesised via the Grignard coupling of protected bromohydrins with alkylcuprate as a key step. The synthesis of 8-methyldec-2-yl propanoate (I), the northern corn rootworm Diabrotica longicornis Say pheromone, was achieved from pentane-1,5-diol in four steps with an overall yield of 35.1 % and 10-methyltridecan-2-one (II), the southern corn rootworm Diabrotica undecimpunctata howardi Barber pheromone, was synthesised from octane-1,8-diol as commercially available starting material in five steps with an overall yield of 28.7 %. |
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