Total synthesis of (-)-periplanones C and D. Their pheromonal activities against three Periplaneta species

Article abstract of DOI:10.1016/S0040-4020(97)00424-9

Total synthesis of(-)-periplanones C [(-)-PC; 1] and D [(-)-PD; 2] was achieved starting from (-)-germacrene D via 7 and 8 steps, respectively, according to the similar route on syntheses of racemic PC and PD. The ¹H NMR and GC mass spectra of 2 unambiguously determined the structure of the natural sample of PD which was isolated from Periplaneta fuliginosa. Bioassay of synthetic samples of 1 and 2 was carried oat against males of P. fuliginosa, P. americana, and P. japonica. 10^-9 g of 1 elicited significant response in males of P. americana and P. japonica. 10^-10 g of 2 elicited strong response in P. fuliginosa males, whereas it showed significantly weak response against males of P. americana and P. japonica. Almost same degree of activities was observed between 1 and 2 against males of P. americana and P. japonica at 10^-10 g dose.