New synthesis of the (3Z,6Z,9S,10R)-isomers of 9,10-epoxy-3,6-henicosadiene and 9,10-epoxy-1,3,6-henicosatriene, pheromone components of the female fall webworm moth, Hyphantria cunea.
(3Z,6Z,9S,10R)-9,10-Epoxy-3,6-henicosadiene (1) and (3Z,6Z,9S,10R)-9,10-epoxy-1,3,6-henicosatriene (5), pheromone components of the female fall webworm moth (Hyphantria cunea Drury), were synthesized by starting from (2S,3R)-2,3-epoxy-4-t-butyldimethylsilyloxy-1-butanol (8). Epoxide 8 was prepared by employing lipase-catalyzed asymmetric acetylation of (+/-)-8 as the key optical resolution step.
Nakanishi
Akira
A
Department of Applied Biological Chemistry, The University of Tokyo, Tokyo.
Mori
Kenji
K
D000818:Animals; D004852:Epoxy Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D005231:Fatty Acids, Unsaturated / Q000138:chemical synthesis* / Q000737:chemistry; D005260:Female; D015394:Molecular Structure; D009036:Moths / Q000737:chemistry*; D012724:Sex Attractants / 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; D012724:Sex Attractants