Pityogenes chalcographus

Birgersson G., Byers J.A., Bergstrom G. and Lofqvist J. (1990) Production of pheromone components, chalcogran and methyl ( ,Z)-2,4-decadienoate, in the spruce engraver Pityogenes chalcographus. J. Insect Physiol. 36, 391-395. 

Francke W., Heeman V., Gerken B., Renwick J. A. A. and Vite J. P. (1977) 2-Ethyl-l,6-dioxaspiro[4.4]nonane, principal aggregation pheromone of Pityogenes chalcographus (L.). Naturwissenschaften 64, 590. 

Figure 7. Pheromones from R or S lactone acid for beetles dermestids (y-capro-lactone), Pityogenes chalcographus (L.), Japanese beetle (I, Fig. 1), ambrosia beetle, and lesser grain borer beetle gypsy moths and block-tailed deer.

Baeckstrom, P., Jacobsson, U., Norin, T., and UneUus, C.R., Synthesis and characterization of all four isomers of methyl 2,4-decadienoate for an investigation of the pheromone components of Pityogenes chalcographus. Tetrahedron, 44, 2541, 1988. 

Other spiroacetal natural products have been prepared using malic acid-derived epoxides as the chiral source (Scheme 54). Chalcogran (407, R=CH3, = 1) is the principal component of the aggregation pheromone of the beetle Pityogenes chalcographus (L.), a pest of Norway spruce. Spiroacetal 407 (R—H, = 2) is a minor volatile component found in the common wasp, Paravespula vulgaris. 

Treatment of the 1,5-diene (Z,Z)-CHD=CHCH2CH2CH=CHD with potassium permanganate results in stereospecific oxidative cycloaddition to give 40% of the tetrahydrofuran (25), which possesses four chiral centres the (E,E)-isomer behaves in an analogous fashion. " 2,2-Dialkoxytetrahydrofurans are formed from epoxides and keten acetals thus epichlorhydrin reacts with MeCH=C(OMe)2 in the presence of zinc chloride to afford compound (26). The chloro-furanone (27) is obtained as a mixture of cis- and trans-isomers from styrene and trimethylsilyl dichloroacetate in the presence of bis(triphenylphos-phine)ruthenium(ii) chloride. Total syntheses of both enantiomers of the pheromone (28) of the Japanese beetle [Popillia japonica) and of chalcogran (29), the principal pheromone of Pityogenes chalcographus (L.), have been described. 

Francke et al (632) identiried spiroacetal (627) as an aggregation pheromone in the bark beetle Pityogenes chalcographus. 

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