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Synthesis of corn rootworm pheromones from commercial diols

Thanh-Danh Nguyen, Cong-Hao Nguyen, Chan Im, and Chi-Hien Dang

Department of Pharmaceutical Chemistry Technology, Institute of Chemical Technology, Vietnam Academy of Science and Technology, 1 Mac Dinh Chi Street, District 1, Ho Chi Minh City, Vietnam

 

E-mail: danh5463bd@yahoo.com

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 %.

Keywords: Diabrotica longicornis Say – Diabrotica undecimpunctata howardi Barber – Grignard coupling – pheromone – bromohydrin – diol

Full paper is available at www.springerlink.com.

DOI: 10.1515/chempap-2015-0027

 

Chemical Papers 69 (2) 380–384 (2015)

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