Synthesis of the sex pheromone of the citrus mealybug, Pseudococcus cryptus.
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.
Nakahata
Takashi
T
Laboratory of Applied Bioorganic Chemistry, Division of Life Science, Graduate School of Agricultural Science, Tohoku University, Sendai, Japan.
Itagaki
Noriaki
N
Arai
Tomonori
T
Sugie
Hajime
H
Kuwahara
Shigefumi
S
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*
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