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J Org Chem


Title:"A concise, protection-free and divergent approach for the enantioselective syntheses of two pheromonal epoxide components of the fall webworm moth and other species"
Author(s):Du Y; Zheng JF; Wang ZG; Jiang LJ; Ruan YP; Huang PQ;
Address:"Department of Chemistry and Key Laboratory for Chemical Biology of Fujian Province, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian 361005, People's Republic of China"
Journal Title:J Org Chem
Year:2010
Volume:75
Issue:13
Page Number:4619 - 4622
DOI: 10.1021/jo1007042
ISSN/ISBN:1520-6904 (Electronic) 0022-3263 (Linking)
Abstract:"On the basis of Zhou's modified Sharpless asymmetric epoxidation, sequential coupling reactions, and a divergent strategy, the protection-free syntheses of two main pheromonal components 1 and 5, found in the fall webworm moth, Hyphantria cunea, and other species have been accomplished in 10 steps (for two compounds). The overall yields are 31% for 1, 28% for 5, and 25% for both 1 and 5, respectively. The ee values of the final products 1 and 5 are at least 99%"
Keywords:"Animals Epoxy Compounds/*chemical synthesis/chemistry Fatty Acids, Unsaturated/*chemical synthesis/chemistry Molecular Structure Moths Pheromones/*chemical synthesis/chemistry Stereoisomerism;"
Notes:"MedlineDu, Yu Zheng, Jian-Feng Wang, Zhi-Gang Jiang, Li-Jiao Ruan, Yuan-Ping Huang, Pei-Qiang eng Research Support, Non-U.S. Gov't 2010/05/29 J Org Chem. 2010 Jul 2; 75(13):4619-22. doi: 10.1021/jo1007042"

 
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