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Volumn 65, Issue 6, 2001, Pages 1429-1433

New synthesis of serricornin, the female sex pheromone of the cigarette beetle

Author keywords

Asymmetric synthesis; Cigarette beetle; Pheromone; Serricornin

Indexed keywords

COLEOPTERA; LASIODERMA SERRICORNE;

EID: 0035380246     PISSN: 09168451     EISSN: None     Source Type: Journal    
DOI: 10.1271/bbb.65.1429     Document Type: Article
Times cited : (8)

References (23)
  • 1
    • 0018391099 scopus 로고
    • 4,6-Dimethyl-7-hydroxynonan-3-one, a sex pheromone of cigarette beetle (Lasioderma serricorne F.)
    • Chuman, T., Kohno, M., Kato, K., and Noguchi, M., 4,6-Dimethyl-7-hydroxynonan-3-one, a sex pheromone of cigarette beetle (Lasioderma serricorne F.). Tetrahedron Lett., 25, 2361-2364 (1979).
    • (1979) Tetrahedron Lett. , vol.25 , pp. 2361-2364
    • Chuman, T.1    Kohno, M.2    Kato, K.3    Noguchi, M.4
  • 2
    • 34250120889 scopus 로고
    • Lasioderma chemistry. Sex pheromone of cigarette beetle ( Lasioderma serricorne F.)
    • Chuman, T., Mochizuki, K., Mori, M., Kohno, M., Kato, K., and Noguchi, M., Lasioderma chemistry. Sex pheromone of cigarette beetle ( Lasioderma serricorne F.). J. Chem. Ecol., 11, 417-434 (1985).
    • (1985) J. Chem. Ecol. , vol.11 , pp. 417-434
    • Chuman, T.1    Mochizuki, K.2    Mori, M.3    Kohno, M.4    Kato, K.5    Noguchi, M.6
  • 3
    • 0020263079 scopus 로고
    • Synthesis and absolute stereochemistry of serricornin [(4S,6S,7S)-4,6-dimethyl-7-hydroxy-3-nonanone], the sex pheromone of the cigarette beetle
    • Mori, K., Nomi, H., Chuman, T., Kohno, M., Kato, K., and Noguchi, M., Synthesis and absolute stereochemistry of serricornin [(4S,6S,7S)-4,6-dimethyl-7-hydroxy-3-nonanone], the sex pheromone of the cigarette beetle. Tetrahedron, 38, 3705-3711 (1982).
    • (1982) Tetrahedron , vol.38 , pp. 3705-3711
    • Mori, K.1    Nomi, H.2    Chuman, T.3    Kohno, M.4    Kato, K.5    Noguchi, M.6
  • 4
    • 0000416205 scopus 로고
    • The synthesis of insect pheromones, 1979-1989
    • ed. ApSimon, J., John Wiley, New York
    • Mori, K., The Synthesis of Insect Pheromones, 1979-1989. In "The Total Synthesis of Natural Products" Vol. 9, ed. ApSimon, J., John Wiley, New York, pp. 193-201 (1992).
    • (1992) The Total Synthesis of Natural Products , vol.9 , pp. 193-201
    • Mori, K.1
  • 5
    • 0009508227 scopus 로고
    • Inhibitory action of (4S,6S,7R)-isomer to pheromonal activity of serricornin, (4S,6S,7S)-7-hydroxy-4,6-dimethyl-3-nonanone
    • Mori, M., Mochizuki, K., Kohno, Chuman, T., Ohnishi, A., Watanabe, H., and Mori, K., Inhibitory action of (4S,6S,7R)-isomer to pheromonal activity of serricornin, (4S,6S,7S)-7-hydroxy-4,6-dimethyl-3-nonanone. J. Chem. Ecol., 12, 83-89 (1986).
    • (1986) J. Chem. Ecol. , vol.12 , pp. 83-89
    • Mori, M.1    Mochizuki, K.2    Kohno3    Chuman, T.4    Ohnishi, A.5    Watanabe, H.6    Mori, K.7
  • 6
    • 0000133961 scopus 로고
    • Bornanesultam-directed asymmetric synthesis of crystalline enantiomerically pure syn aldols
    • Oppolzer, W., Blagg, J., Rodriguez, J., and Walther, E., Bornanesultam-directed asymmetric synthesis of crystalline enantiomerically pure syn aldols. J. Am. Chem. Soc., 112, 2767-2772 (1990).
    • (1990) J. Am. Chem. Soc. , vol.112 , pp. 2767-2772
    • Oppolzer, W.1    Blagg, J.2    Rodriguez, J.3    Walther, E.4
  • 7
    • 0026090715 scopus 로고
    • Facile synthesis of (-)-serricornin by means of palladium-catalyzed hydrogenolysis of alkenyloxiranes
    • Shimizu, J., Hayashi, K., Ide, N., and Oshima, M., Facile synthesis of (-)-serricornin by means of palladium-catalyzed hydrogenolysis of alkenyloxiranes. Tetrahedron, 47, 2991-2998 (1991).
    • (1991) Tetrahedron , vol.47 , pp. 2991-2998
    • Shimizu, J.1    Hayashi, K.2    Ide, N.3    Oshima, M.4
  • 8
    • 0042411689 scopus 로고
    • New stereocontrolled approach to the insect sex pheromone serricornin
    • Szurdoki, F., Novák, L., Baitz-Gács, E., and Szántay, C., New stereocontrolled approach to the insect sex pheromone serricornin. Acta Chem. Hungarica, 129, 303-309 (1992).
    • (1992) Acta Chem. Hungarica , vol.129 , pp. 303-309
    • Szurdoki, F.1    Novák, L.2    Baitz-Gács, E.3    Szántay, C.4
  • 9
    • 0027239699 scopus 로고
    • Enantioselective synthesis of (-)-serricornin, a sex pheromone of female cigarete beetle (Lasioderma serricorne F.)
    • Miyashita, M., Toshimitsu, Y., Shiratani, T., and Irie, H., Enantioselective synthesis of (-)-serricornin, a sex pheromone of female cigarete beetle (Lasioderma serricorne F.). Tetrahedron: Asymmetry, 4, 1573-1578 (1993).
    • (1993) Tetrahedron: Asymmetry , vol.4 , pp. 1573-1578
    • Miyashita, M.1    Toshimitsu, Y.2    Shiratani, T.3    Irie, H.4
  • 10
    • 0028265766 scopus 로고
    • A short formal synthesis of (-)-serricornin
    • Pilli, R. A., and de Andrade, C. K. Z., A short formal synthesis of (-)-serricornin. Synth. Commun., 24, 233-241 (1994).
    • (1994) Synth. Commun. , vol.24 , pp. 233-241
    • Pilli, R.A.1    De Andrade, C.K.Z.2
  • 11
    • 0028345692 scopus 로고
    • A formal and enantioselective synthesis of (-)-serricornin, the sex pheromone of the cigarette beetle (Lasioderma serricorne)
    • Ferreira, J. T. B., Marques, J. A., and Marius, J. P., A formal and enantioselective synthesis of (-)-serricornin, the sex pheromone of the cigarette beetle (Lasioderma serricorne). Tetrahedron: Asymmetry, 5, 641-648 (1994).
    • (1994) Tetrahedron: Asymmetry , vol.5 , pp. 641-648
    • Ferreira, J.T.B.1    Marques, J.A.2    Marius, J.P.3
  • 12
    • 0028329863 scopus 로고
    • A practical enantioselective synthesis of the cigarette beetle sex pheromone serricornin
    • Chan, P. C. -M., Chong, J. M., and Kousha, K., A practical enantioselective synthesis of the cigarette beetle sex pheromone serricornin, Tetrahedron, 50, 2703-2714 (1994).
    • (1994) Tetrahedron , vol.50 , pp. 2703-2714
    • Chan, P.C.-M.1    Chong, J.M.2    Kousha, K.3
  • 13
    • 0032261451 scopus 로고    scopus 로고
    • A chemoenzymatic synthesis of the sex pheromone of Lasioderma serricorne F
    • Pilli, R. A., and Riatto, V. B., A chemoenzymatic synthesis of the sex pheromone of Lasioderma serricorne F. J. Brazil. Chem. Soc., 9, 571-576 (1998).
    • (1998) J. Brazil. Chem. Soc. , vol.9 , pp. 571-576
    • Pilli, R.A.1    Riatto, V.B.2
  • 14
    • 0001379333 scopus 로고    scopus 로고
    • Asymmetric synthesis of serricornin via boronic esters
    • Matteson, D. S., Singh, R. P., Sehafman, B., and Yang, J. -i., Asymmetric synthesis of serricornin via boronic esters. J. Org. Chem., 63, 4466-4469 (1998).
    • (1998) J. Org. Chem. , vol.63 , pp. 4466-4469
    • Matteson, D.S.1    Singh, R.P.2    Sehafman, B.3    Yang, J.-I.4
  • 15
    • 0032808807 scopus 로고    scopus 로고
    • The baker's yeast reduction of the β-keto aldehydes in the presence of a sulfur compound
    • Hayakawa, R., and Shimizu, M., The baker's yeast reduction of the β-keto aldehydes in the presence of a sulfur compound. Synlett, 1298-1300 (1999).
    • (1999) Synlett , pp. 1298-1300
    • Hayakawa, R.1    Shimizu, M.2
  • 16
    • 0035144339 scopus 로고    scopus 로고
    • Pheromone synthesis, CCVI. Synthesis of (2R,4R)-supellapyrone, the sex pheromone of the brownbanded cockroach, Supella longipalpa, and its three stereoisomers
    • Fujita, K., and Mori, K., Pheromone synthesis, CCVI. Synthesis of (2R,4R)-supellapyrone, the sex pheromone of the brownbanded cockroach, Supella longipalpa, and its three stereoisomers. Eur. J. Org. Chem., 493-502 (2001).
    • (2001) Eur. J. Org. Chem. , pp. 493-502
    • Fujita, K.1    Mori, K.2
  • 18
    • 0032854921 scopus 로고    scopus 로고
    • Pheromone synthesis, CXCVIII. Synthesis of (1S,2S,6S,10R)- and (1S, 2R,6R,10R)-1,2,6,10-tetramethyldodecyl propionate, the components of the sex pheromone of the pine sawfly, Microdiprion pallipes
    • Nakamura, Y., and Mori, K., Pheromone synthesis, CXCVIII. Synthesis of (1S,2S,6S,10R)- and (1S, 2R,6R,10R)-1,2,6,10-tetramethyldodecyl propionate, the components of the sex pheromone of the pine sawfly, Microdiprion pallipes. Eur. J. Org. Chem., 2175-2182 (1999).
    • (1999) Eur. J. Org. Chem. , pp. 2175-2182
    • Nakamura, Y.1    Mori, K.2
  • 19
    • 0042939482 scopus 로고
    • Diastereo- and enantioselective preparation of β-alkylhomoallylic alcohols
    • Kobayashi, Y., Kitano, Y., Takeda, Y., and Sato, F., Diastereo- and enantioselective preparation of β-alkylhomoallylic alcohols. Tetrahedron, 42, 2937-2943 (1986).
    • (1986) Tetrahedron , vol.42 , pp. 2937-2943
    • Kobayashi, Y.1    Kitano, Y.2    Takeda, Y.3    Sato, F.4
  • 20
    • 0041409342 scopus 로고
    • Enantiocontrolled approach to natural products utilizing (S)-O-benzylglycidol as common chiral precursor
    • Takano, S., Sekiguchi, Y., and Ogasawara, K., Enantiocontrolled approach to natural products utilizing (S)-O-benzylglycidol as common chiral precursor. Heterocycles, 29, 445-448 (1989).
    • (1989) Heterocycles , vol.29 , pp. 445-448
    • Takano, S.1    Sekiguchi, Y.2    Ogasawara, K.3
  • 21
    • 0001631004 scopus 로고
    • Electrophilic lactonization as a tool in acyclic stereocontrol. Synthesis of serricornin
    • Bartlett, P. A., Richardson, D. P., and Meyerson, J., Electrophilic lactonization as a tool in acyclic stereocontrol. Synthesis of serricornin. Tetrahedron, 40, 2317-2327 (1984).
    • (1984) Tetrahedron , vol.40 , pp. 2317-2327
    • Bartlett, P.A.1    Richardson, D.P.2    Meyerson, J.3
  • 22
    • 0000935128 scopus 로고
    • Synthesis of optically active insect pheromones. (2R,5S)-2-methyl-5-hexanolide, (3S,11S)-3,11-dimethyl-2-nonacosanone, and serricornin
    • Katsuki, T., and Yamaguchi, M., Synthesis of optically active insect pheromones. (2R,5S)-2-methyl-5-hexanolide, (3S,11S)-3,11-dimethyl-2-nonacosanone, and serricornin. Tetrahedron Lett., 28, 651-654 (1987).
    • (1987) Tetrahedron Lett. , vol.28 , pp. 651-654
    • Katsuki, T.1    Yamaguchi, M.2
  • 23
    • 0003016674 scopus 로고
    • Pheromone synthesis, LXVI. A new synthesis of serricornin [(4S,6S,7S)-7-hydroxy-4,6-dimethyl-3-nonanone], the sex pheromone of the cigarette beetle
    • Mori, K., and Watanabe, H., Pheromone synthesis, LXVI. A new synthesis of serricornin [(4S,6S,7S)-7-hydroxy-4,6-dimethyl-3-nonanone], the sex pheromone of the cigarette beetle. Tetrahedron, 41, 3423-3428 (1985).
    • (1985) Tetrahedron , vol.4 , pp. 13423-13428
    • Mori, K.1    Watanabe, H.2


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