Supella longipalpa pheromone

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 ... 

Schal, C., Liang, D., Hazarika, L. K., Charlton, R. E. and Roelofs, W. L. (1992). Site of pheromone production in female Supella longipalpa (Dictyoptera Blattellidae) behavioral, electrophysiological, and morphological evidence. Annals of the Entomological Society of America 85 605-611. 

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. 

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... 

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