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.
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%.
authors.affiliation: 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.
authors.forename: Yu
authors.initials: Y
authors.lastname: Du
authors.forename: Jian-Feng
authors.initials: JF
authors.lastname: Zheng
authors.forename: Zhi-Gang
authors.initials: ZG
authors.lastname: Wang
authors.forename: Li-Jiao
authors.initials: LJ
authors.lastname: Jiang
authors.forename: Yuan-Ping
authors.initials: YP
authors.lastname: Ruan
authors.forename: Pei-Qiang
authors.initials: PQ
authors.lastname: Huang
mesh_terms: D000818:Animals; D004852:Epoxy Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D005231:Fatty Acids, Unsaturated / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009036:Moths; D010675:Pheromones / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: C503269:9,10-epoxy-1,3,6-henicosatriene; C503270:9,10-epoxy-3,6-henicosadiene; D004852:Epoxy Compounds; D005231:Fatty Acids, Unsaturated; D010675:Pheromones