Dendroctonus ponderosae Brevicomin

Figure 6.12 Cyclization reactions of acyclic, unbranched and methyl-branched ketones to bicyclic acetals and cyclic alcohols in bark beetles. (A) Mountain pine beetle, Dendroctonus ponderosae formation of exo-brevicomin [(1 F ,5S,7fl)-(+)-7-ethyl-5-methyl-6,8-dioxabicyclo[3.2.1]octane] from (Z)-6-nonen-2-one (Vanderwel and Oehlschlager, 1992 Vanderwel ef a/., 1992a) ...

Ryker L. C. and Rudinsky J. A. (1982) Field bioassay of exo- and endo-brevicomin with Dendroctonus ponderosae in lodgepole pine. J. Chem. Ecol. 8, 701-707. 

Successful host colonization depends on recruiting a minimum number of Dendroctonus pon-derosae to attack the tree and overcome its defenses," a process that is completed within 2-3 weeks. As the abundance of colonizing male Dendroctonus ponderosae increases, levels of male-secreted cxo-brevicomin and frontalin increase " " - while concentrations of the aggregation pheromones trans- and cis-verbenol and host monoterpenes decline."" This reduces the attractiveness of the target tree and commences latter stages of tree colonization. The secretion of 2-phenylethanol by males" " and the release of l-octen-3-ol by females may further reduce attraction to the target tree. 

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