Rhagoletis cerasi Oviposition deterring pheromones

Treatment of bromide 454b with magnesium generates Grignard reagent 495 [114], which is readily alkylated with bromide 496. Acetonide 497 was subsequently converted to 498, the oviposition-deterring pheromone of Rhagoletis cerasi L. (Scheme 70). 

The European cherry fruit fly, Rhagoletis cerasi, lays a single egg into half-ripe cherries. An oviposition-deterring pheromone, which prevents oviposition by a second female of the same species, was isolated from the feces of the insect. This compound was characterized as A [15(p-glucosyl)oxy-8-hydroxypalmitoyl]-taurine (76) (Fig. 2.30) (Hurter et al., 1987). 

Hurter, J., E. F. Boller, E. Stadler, B. Blattmann, H. R. Buser, N. U. Bosshard, L. Damm, M. W. Kozlowski, R. ScHONi, F. Raschdorf, R. Dahinden, E. Schlumpf, H. Fritz, W. J. Richter, and J. Schreiber, Oviposition-deterring pheromone in Rhagoletis cerasi L. Purification and determination of the chemical constitution, Experientia, 43, 157-164 (1987). 

Boiler, E.F. J. Horter. 1985. Oviposition deterring pheromone in Rhagoletis cerasi behavioral laboratory test to measure pheromone activity. Entomol. Exp. Appl. 39 163-169. 

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