Tetrahedron p. 7209 - 7218 (1997)
Update date:2022-08-16
Topics:
Nishii, Yoshinori
Watanabe, Keisuke
Yoshida, Taichi
Okayama, Tatsutoshi
Takahashi, Shozo
Tanabe, Yoo
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.
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Doi:10.1039/c3ra45315d
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(1969)Doi:10.1039/d0cc07632e
(2021)Doi:10.1021/ja01613a061
(1955)Doi:10.1039/c5cc03087k
(2015)Doi:10.1007/BF00479936
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