Supella longipalpa Cockroaches

R,4R)-Supellapyrone (41) is the female sex pheromone of the brown banded cockroach (Supella longipalpa). Scheme 59 summarizes Mori s synthesis of 41 [89].Enzymatic desymmetrization of meso-B to give (2R,4S)-C and Reformatsky-type cyclization of D to furnish E were the key steps. 

Lipase-catalyzed desymmetrization was used to synthesize supellapyrone and its three stereoisomers, the female sex pheromone of the brown-banded cockroach Supella longipalpa ... 

Hales, R. A. and Breed, M. D. (1983). Female calling and reproductive behavior in the brown banded cockroach, Supella longipalpa (F.) (Orthoptera Blattellidae). Annals of the Entomological Society of America 76 239-241. 

Smith, A. F. and Schal, C. (1990a). Corpus allatum control of sex pheromone production and calling in the female brown-banded cockroach, Supella longipalpa (F.) (Dictyoptera Blattellidae). Journal of Insect Physiology 36 251-257. 

Smith A. F., Yagi K., Tobe S. S. and Schal C. (1989) In vitro juvenile hormone biosynthesis in adult virgin and mated female brown-banded cockroaches, Supella longipalpa. J. Insect Physiol. 35, 781-785. 

In 1993 Roelofs and coworkers in the USA isolated and identified supellapyrone (115, Figure 4.73) as the female-produced sex pheromone of the brownbanded cockroach (Supella longipalpa). Meinwald proposed its stereochemistry as 27 ,47 . After preparing (27 , 47 )-115128 and (27 ,47 )-115,129 we synthesized all of the four stereoisomers of 115 as shown in Figure 4.73.130... 

Fig. (3). Juvenile hormone III (JH III) release from the corpora allata (CA) of the oviparous cockroach, Supella longipalpa [48]. Juvenile hormone release was measured by the in vitro radiochemical assay [49, 50] and values represent the means of 5-12 determinations. Approximate times of mating and oviposition are indicated by arrows (reprinted with kind permission from Elsevier Scientific).

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