Synthesis of the female sex pheromone of the citrus mealybug, Planococcus citri.
The citrus mealybug, Planococcus citri (Risso) is a common pest in the Southern U. S. and the Mediterranean. Two alternative syntheses of the female sex pheromone, (1R)-(+)-cis-2,2-dimethyl-3-isopropenyl-cyclobutane methanol acetate, have been developed. Key transformations include an allylic oxidation of (1R)-(+)-alpha-pinene to (+)-R-verbenone, oxidative decarboxylation using RuCl(3)-NaIO(4), and methylenation with Zn/CH(2)Br(2)/TiCl(4).
Passaro
Linda C
LC
Center for Bio/Molecular Science and Engineering, Naval Research Laboratory, Washington, DC 20375, USA.
Webster
Francis X
FX
D000818:Animals; D002957:Citrus; D006430:Hemiptera / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D012724:Sex Attractants / Q000138:chemical synthesis*
D012724:Sex Attractants