Synthesis of the Female Sex Pheromone of the Citrus Mealybug, Planococcus citri
Journal of Agricultural and Food Chemistry2004Vol. 52(10), pp. 2896–2899
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Abstract
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)-(+)-α-pinene to (+)-R-verbenone, oxidative decarboxylation using RuCl3−NaIO4, and methylenation with Zn/CH2Br2/TiCl4. Keywords: (+)-cis-Planococcyl acetate; synthesis; pheromones; olefination; oxidation
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