title: Synthesis of the sex pheromone of the citrus mealybug, Pseudococcus cryptus.
abstract: 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.
authors.affiliation: Laboratory of Applied Bioorganic Chemistry, Division of Life Science, Graduate School of Agricultural Science, Tohoku University, Sendai, Japan.
authors.forename: Takashi
authors.initials: T
authors.lastname: Nakahata
authors.forename: Noriaki
authors.initials: N
authors.lastname: Itagaki
authors.forename: Tomonori
authors.initials: T
authors.lastname: Arai
authors.forename: Hajime
authors.initials: H
authors.lastname: Sugie
authors.forename: Shigefumi
authors.initials: S
authors.lastname: Kuwahara
mesh_terms: D000818:Animals; D000081008:Bicyclic Monoterpenes; D002087:Butyrates / Q000138:chemical synthesis*; D003503:Cyclobutanes / Q000138:chemical synthesis*; D006430:Hemiptera / Q000378:metabolism*; D039821:Monoterpenes / Q000138:chemical synthesis / Q000737:chemistry*; D012724:Sex Attractants / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: C482762:3-isopropenyl-2,2-dimethylcyclobutylmethyl 3-methyl-3-butenoate; D000081008:Bicyclic Monoterpenes; D002087:Butyrates; D003503:Cyclobutanes; D039821:Monoterpenes; D012724:Sex Attractants; C005451:alpha-pinene