Marzo Bargues, J., Vacas, S., Navarro Fuertes, I., Primo, J., Abad-Somovilla, A., & Navarro-Llopis, V. 2024 Absolute Configuration of the Invasive Mealybug Delottococcus aberiae (De Lotto) Sex Pheromone: Synthesis and Bioassay of Both Enantiomers. Journal of Agricultural and Food Chemistry https://doi.org/10.1021/acs.jafc.4c05469
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Notes: In a previous work, (4,5,5-trimethyl-3-methylenecyclopent-1-en-1-yl)methyl acetate was identified as the sex pheromone emitted by females, a new compound with an unusual β-necrodol skeleton possessing one stereocenter. This compound was assigned to the (−)-enantiomer but the absolute configuration was then not reported. In the present study, enantiomeric pure samples of both enantiomers were synthesized. X-ray diffraction analysis allowed the (−)-enantiomer, identical to the one emitted by virgin D. aberiae females, to be unequivocally identified as (−)-(R)-(4,5,5-trimethyl-3-methylenecyclopent-1-en-1-yl)methyl acetate. Bioassays carried out to test the activity of both enantiomers under field conditions suggest that the presence of the (+)-(S)-enantiomer has detrimental effects on the activity of the racemates.
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