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The sex pheromone of the citrus mealybug (Pseudococcus cryptus), [(1R,3R)-3-isopropenyl-2,2-dimethylcyclobutyl]methyl 3-methyl-3-butenoate, was synthesized from (+)-alpha-pinene in five operational steps in a 43% overall yield. The synthetic pheromone was identical with the natural pheromone in (1)H-NMR and mass spectroscopic properties, and showed almost the same pheromonal activity as the natural pheromone.
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Nakahata et al. (2003) studied this question.
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