Antiaggregative pheromone

Libbey L. M., Morgan M. E., Putnam T. B. and Rudinsky J. A. (1976) Isomer of antiaggregation pheromone identified from male Douglas-fir beetle 3-methylcyclohex-3-en-l-one. J. Insect Physiol. 22, 871-873. 

Ethyl-2-methyl-l,6-dioxaspiro[4.5]decane is a constituent of the antiaggregative pheromone produced by several varieties of bees. All of the four thermodynamically stable stereoisomers of this spiroacetal have been synthesized using (5)-malic acid and (5)-lactic acid as the sources of chirality [15]. 

Kostyk, B. C., J. H. Borden, and G. Gries, Photoisomerization of antiaggregation pheromone verbenone Biological and practical implications with respect to the mountain pine beetle, Dendroctonus ponderosae Hopkins (Coleoptera Scolytidae)./. Chem. Ecol. 19 1749-1759, 1993. 

Rudinsky, J. A. et al. Antiaggregative-rivalry pheromone of the mountain pine beetle, and a new arrestant... 

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