TOTAL SYNTHESIS OF (-)-PERIPLANONE-C AND (-)-PERIPLANONE-D - THEIR PHEROMONAL ACTIVITIES AGAINST 3 PERIPLANETA SPECIES

Total synthesis of(-)-periplanones C [(-)-PC; 1] and D [(-)-PD; 2] was achieved starting from (-)-germacrene D via 7 and 8 steps, respective ly, according to the similar route on syntheses of racemic PC and PD. The H-1 NMR and GC mass spectra of 2 unambiguously determined the stru cture of the natural sample of PD which was isolated from Periplaneta fuliginosa. Bioassay of synthetic samples of 1 and 2 was carried out a gainst males of P. fuliginosa, P. americana, and P. japonica. 10(-9) g of 1 elicited significant response in males of P. americana and P. ja ponica. 10(-10) g of 2 elicited strong response in P. fuliginosa males , whereas it showed significantly weak response against males of P. am ericana 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. (C) 1997 Published by Elsevier Science Ltd.