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Compound - periplanone-B [(1Z,5E)-1,10(14)-Diepoxy-4(15),5-germacradien-9-one]

Bedoukain RussellIPM
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Formula: C15H20O3 
CAS#: 61228-92-0 
MW: 248.32 

[MS]  [ NMR ]  [Behavioural function

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Reference(s) for synthesis of (1Z,5E)-1,10(14)-Diepoxy-4(15),5-germacradien-9-one [periplanone-B]

Adams, M.A., Nakanishi, K., Still, W.C., Arnold, E.V., Clardy, J., and Persoons, C.J. 1979. Sex pheromone of the American Cockroach: absolute configuration of Periplanone-B. J. Am. Chem. Soc. 101:2495-2498.
Hauptmann, H. and Muehlbauer, G. 1986. Synthese und Krystallstruktur von (+)-Periplanon B. Tetrahedron Lett. 27:1315-1318.
Kitahara, T., Mori, M., and Mori, K. 1987. Total synthesis of (-)-Periplanone-B, natural major sex-excitant pheromone of the American cockroach, Periplaneta americana. Tetrahedron. 43:2689-2699.
Kitahara, T., Mori, M., Koseki, K., and Mori, K. 1986. Total synthesis of (-)-Periplanone-B, the sex pheromone of the American cockroach. Tetrahedron Lett. 27:1343-1346.
Kuwahara, S., and Mori, K. 1990. Synthesis of (-)-periplanone-B, a sex pheromone component of the American cockroach (Periplaneta americana). Tetrahedron. 46:8075-8082.
Niwa, M., Iguchi, M., and Yamamura, S. 1978. Biomimetic reactions of epoxygermacrene-D. Tetrahedron Lett. 42:4043-4046.
Niwa, M., Iguchi, M., and Yamamura, S. 1984. Co-occurrence of (-) and (+)-germacrene-D in Solidago altissima L.: determination of the optical rotation of optically pure germacrene-D. Chem. Pharm. Bull. 28:997.
Schreiber, S.L. 1985. [2+2] Photocycloadditions in the synthesis of chiral molecules. Science. 227:857.
Schreiber, S.L., and Santini, C. 1984. Cyclobutene bridgehead olefin route to the American cockroach sex pheromone, Periplanone-B. J. Am. Chem. Soc. 106:4038-4039.
Still, W.C. 1979. ()-Periplanone-B, total synthesis and structure of the sex excitant pheromone of the American cockroach. J. Am. Chem. Soc. 101:2493-2495.
Takahashi, S., Kitamura, C., and Horibe, I. 1978. Sex stimulant activity of sesquiterpenes to the males of the American cockroach. Agric. Biol. Chem. 42:79.
Takahashi, T., Kanda, Y., Nemota, H., Kitamura, K., Tsui, J., and Fukazawa, Y. 1986. Stereocontrolled synthesis of American cockroach sex pheromone, Periplanone B. J. Org. Chem. 51:3393-3394.

Citation: El-Sayed AM 2024. The Pherobase: Database of Pheromones and Semiochemicals. <>.
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