| Title: | Asymmetric Total Synthesis of Four Stereoisomers of the Sex Pheromone of the Western Corn Rootworm |
| Author(s): | Sun ZF; Zhang T; Liu J; Du ZT; Zheng H; |
| Address: | "Shaanxi Key Laboratory of Natural Products and Chemical Biology, College of Chemistry and Pharmacy, North West Agriculture and Forestry University, Yangling 712100, China. sunzhifeng2018@163.com. Shaanxi Key Laboratory for Catalysis, College of Chemical and Environment Science, Shaanxi University of Technology, Hanzhong 723001, China. sunzhifeng2018@163.com. Shaanxi Key Laboratory of Natural Products and Chemical Biology, College of Chemistry and Pharmacy, North West Agriculture and Forestry University, Yangling 712100, China. fuzitong@163.com. Shaanxi Key Laboratory of Natural Products and Chemical Biology, College of Chemistry and Pharmacy, North West Agriculture and Forestry University, Yangling 712100, China. m17792029896@163.com. Shaanxi Key Laboratory of Natural Products and Chemical Biology, College of Chemistry and Pharmacy, North West Agriculture and Forestry University, Yangling 712100, China. duzt@nwsuaf.edu.cn. Key Laboratory of Botanical Pesticide R&D in Shaanxi Province, Yangling 712100, China. duzt@nwsuaf.edu.cn. Shaanxi Key Laboratory of Natural Products and Chemical Biology, College of Chemistry and Pharmacy, North West Agriculture and Forestry University, Yangling 712100, China. hjzheng@nwsuaf.edu.cn. Key Laboratory of Botanical Pesticide R&D in Shaanxi Province, Yangling 712100, China. hjzheng@nwsuaf.edu.cn" |
| DOI: | 10.3390/molecules23030667 |
| ISSN/ISBN: | 1420-3049 (Electronic) 1420-3049 (Linking) |
| Abstract: | "A convergent synthesis of four stereoisomers of the sex pheromone of the western corn rootworm (8-methyldecan-2-yl propionate, 1) from commercially available chiral starting materials is reported. The key step was Julia-Kocienski olefination between chiral BT-sulfone and chiral aldehyde. This synthetic route provided the four stereoisomers of 1 in 24-29% total yield via a six-step sequence. The simple scale-up strategy provides a new way to achieve the asymmetric synthesis of the sex pheromone" |
| Keywords: | Animals Coleoptera/*metabolism Molecular Structure Propionates/*chemical synthesis/chemistry Sex Attractants/*chemistry Stereoisomerism Evans methylation Julia-Kocienski olefination convergent synthesis pheromone west corn rootworm; |
| Notes: | "MedlineSun, Zhi-Feng Zhang, Tao Liu, Jinyang Du, Zhen-Ting Zheng, Huaiji eng Switzerland 2018/03/16 Molecules. 2018 Mar 15; 23(3):667. doi: 10.3390/molecules23030667" |
