A concise, protection-free and divergent approach for the enantioselective syntheses of two pheromonal epoxide components of the fall webworm moth and other species.
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%.
Du
Yu
Y
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.
Zheng
Jian-Feng
JF
Wang
Zhi-Gang
ZG
Jiang
Li-Jiao
LJ
Ruan
Yuan-Ping
YP
Huang
Pei-Qiang
PQ
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
C503269:9,10-epoxy-1,3,6-henicosatriene; C503270:9,10-epoxy-3,6-henicosadiene; D004852:Epoxy Compounds; D005231:Fatty Acids, Unsaturated; D010675:Pheromones