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 oxidat...

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Bibliographic Details
Published in:Journal of agricultural and food chemistry 2004-05, Vol.52 (10), p.2896-2899
Main Authors: Passaro, Linda C, Webster, Francis X
Format: Article
Language:English
Subjects:
Animals
Biological and medical sciences
Biological control
Citrus
Control
females
Fundamental and applied biological sciences. Psychology
Hemiptera - chemistry
insect pests
Magnetic Resonance Spectroscopy
Phytopathology. Animal pests. Plant and forest protection
Planococcus citri
Protozoa. Invertebrates
Sex Attractants - chemical synthesis
sex pheromones
synthesis
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Summary: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
ISSN:0021-8561
1520-5118
DOI:10.1021/jf035301h