Absolute configuration of Cecropia juvenile hormone.
The absolute configuration of the predominant Cecropia hormone, methyl 12,14-dihomojuvenate, has been determined to be methyl (E,E)-(10R,11S)-(+)-10,11-epoxy-7-ethyl-3,11-dimethyl-2, 6-tridecadienoate (I). The less abundant hormone, methyl 12-homojuvenate, can be presumed by analogy to have the corresponding 3,7,11-trimethyldienoate structure (II). The assignment has been established with microamounts of substance by applying Horeau's method to the glycol derivative (III) of the hormone.The course of the perchloric acid-catalyzed epoxide ring opening of I was checked by conducting the conversion in (18)O-labeled water. It has been ascertained that the configuration at the secondary hydroxyl group of the resulting III remained unchanged. On the other hand, the hydration proceeded with a surprisingly high rate of cis opening.
D000818:Animals; D002855:Chromatography, Thin Layer; D006018:Glycols / Q000032:analysis; D007605:Juvenile Hormones / Q000032:analysis*; D009682:Magnetic Resonance Spectroscopy; D008961:Models, Structural; D009905:Optical Rotatory Dispersion; D010654:Phenylbutyrates / Q000032:analysis; D014197:Trees / Q000032:analysis*
D006018:Glycols; D007605:Juvenile Hormones; D010654:Phenylbutyrates