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Volumn 52, Issue 10, 2004, Pages 2890-2895

Improved Synthesis and Deployment of (2S,3R)-2-(2Z,5Z-Octadienyl)-3-nonyloxirane, a Pheromone of the Pink Moth, Lymantria mathura

Author keywords

(2S,3R) 2 (2Z,5Z octadienyl) 3 nonyloxirane; (3Z,6Z,9S, 10R) 9,10 epoxy 3,6 nonadecadiene; Lymantria mathura; Pheromone; Pink moth; Syntheses

Indexed keywords

1 BROMO 1,4 HEPTADIENE; 1,4 HEPTADIYNYLLITHIUM; 2 IODOMETHYL 3 NONYLOXIRANE; 3 NONYLOXIRANE; ALCOHOL; EPOXIDE; SEX PHEROMONE; UNCLASSIFIED DRUG;

EID: 2442556214     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf035506q     Document Type: Article
Times cited : (7)

References (35)
  • 1
  • 2
    • 0032935688 scopus 로고    scopus 로고
    • Dispersal tendencies of neonate larvae of Lymantria mathura and the Asian form of Lymantria dispar (Lepidoptera: Lymantriidae)
    • Zlotina, M. A.; Mastro, V. C.; Elkinton, J. S.; Leonard, D. E. Dispersal tendencies of neonate larvae of Lymantria mathura and the Asian form of Lymantria dispar (Lepidoptera: Lymantriidae). Environ. Entomol. 1999, 28, 240-245.
    • (1999) Environ. Entomol. , vol.28 , pp. 240-245
    • Zlotina, M.A.1    Mastro, V.C.2    Elkinton, J.S.3    Leonard, D.E.4
  • 5
    • 34250118339 scopus 로고
    • Sex attractants for geometrid and noctuid moths. Field trapping and electroantennographic responses to triene hydrocarbons and monoepoxydiene derivatives
    • Wong, J. W.; Underhill, E. W.; MacKenzie, S. L.; Chisholm, M. D. Sex attractants for geometrid and noctuid moths. Field trapping and electroantennographic responses to triene hydrocarbons and monoepoxydiene derivatives. J. Chem. Ecol. 1985, 11, 727-756.
    • (1985) J. Chem. Ecol. , vol.11 , pp. 727-756
    • Wong, J.W.1    Underhill, E.W.2    MacKenzie, S.L.3    Chisholm, M.D.4
  • 6
    • 0000923977 scopus 로고
    • Syntheses of optically active pheromones with an epoxy ring, (+)-disparlure and both the enantiomers of (3Z,6Z)-cis-9,10-epoxy-3,6-heneicosadiene
    • Mori, K.; Ebata, T. Syntheses of optically active pheromones with an epoxy ring, (+)-disparlure and both the enantiomers of (3Z,6Z)-cis-9,10-epoxy-3,6-heneicosadiene. Tetrahedron 1986, 42, 3471-3478.
    • (1986) Tetrahedron , vol.42 , pp. 3471-3478
    • Mori, K.1    Ebata, T.2
  • 7
    • 84986685698 scopus 로고
    • Synthesis of the enantiomers of (3Z,6Z)-cis-9,10-epoxy-1,3,6-henicosatriene and (3Z,6Z)-cis-9,10-epoxy-1,3,6-icosatriene, the new pheromone components of Hyphantria cunea
    • Mori, K.; Takeuchi, T. Synthesis of the enantiomers of (3Z,6Z)-cis-9,10-epoxy-1,3,6-henicosatriene and (3Z,6Z)-cis-9,10-epoxy-1,3,6-icosatriene, the new pheromone components of Hyphantria cunea. Liebigs Ann. Chem. 1989, 453-457.
    • (1989) Liebigs Ann. Chem. , pp. 453-457
    • Mori, K.1    Takeuchi, T.2
  • 8
    • 0019816531 scopus 로고
    • Synthesis of optically active pheromone with an epoxy ring, (+)-disparlure and the saltmarsh caterpillar moth pheromone [(Z,Z)-3,6-cis-9,10-epoxyheneicosadiene]
    • Mori, K.; Ebata, T. Synthesis of optically active pheromone with an epoxy ring, (+)-disparlure and the saltmarsh caterpillar moth pheromone [(Z,Z)-3,6-cis-9,10-epoxyheneicosadiene]. Tetrahedron Lett. 1981, 22, 4281-4282.
    • (1981) Tetrahedron Lett. , vol.22 , pp. 4281-4282
    • Mori, K.1    Ebata, T.2
  • 9
    • 0012331326 scopus 로고
    • Arachidonate epoxygenase: Total synthesis of both enantiomers of 8,9- and 11,12-epoxyeicosatrienoic acid
    • Mosset, P.; Yadagiri, P.; Lumin, S.; Capdevila, J.; Falk, J. R. Arachidonate epoxygenase: total synthesis of both enantiomers of 8,9- and 11,12-epoxyeicosatrienoic acid. Tetrahedron Lett. 1986, 27, 6035-6038.
    • (1986) Tetrahedron Lett. , vol.27 , pp. 6035-6038
    • Mosset, P.1    Yadagiri, P.2    Lumin, S.3    Capdevila, J.4    Falk, J.R.5
  • 10
    • 0032566061 scopus 로고    scopus 로고
    • Total synthesis of enantiomers of (3Z,6Z)-cis-9,10-epoxy 1,3,6-henicosatriene-the pheromonal component of Diacrisia obliqua
    • Yadav, J. S.; Valli, M. Y.; Prasad, A. R. Total synthesis of enantiomers of (3Z,6Z)-cis-9,10-epoxy 1,3,6-henicosatriene-the pheromonal component of Diacrisia obliqua. Tetrahedron 1998, 54, 7551-7562.
    • (1998) Tetrahedron , vol.54 , pp. 7551-7562
    • Yadav, J.S.1    Valli, M.Y.2    Prasad, A.R.3
  • 11
    • 2442551225 scopus 로고    scopus 로고
    • 2,3-Epoxy derivatives as anti retroviral chemotherapeutic agents. U.S. Patent 5,190,969, 1993
    • Blumenstein, J. J.; Michejda, C. J.; Oroszlan, S.; Copeland, T. 2, 3-Epoxy derivatives as anti retroviral chemotherapeutic agents. U.S. Patent 5,190,969, 1993.
    • Blumenstein, J.J.1    Michejda, C.J.2    Oroszlan, S.3    Copeland, T.4
  • 12
    • 0037164031 scopus 로고    scopus 로고
    • Syntheses of (Z,E)-5,7-dodecadienol and (E,Z)-10,12-hexadecadienol, Lepidoptera pheromone components, via zinc reduction of enyne precursors. Test of pheromone efficacy against the Siberian moth
    • Khrimian, A.; Klun, J. A.; Hijji, Y.; Baranchikov, Y. N.; Pet'ko, V. M.; Mastro, V. C.; Kramer, M. H. Syntheses of (Z,E)-5,7-dodecadienol and (E,Z)-10,12-hexadecadienol, Lepidoptera pheromone components, via zinc reduction of enyne precursors. Test of pheromone efficacy against the Siberian moth. J. Agric. Food Chem. 2002, 50, 6366-6370.
    • (2002) J. Agric. Food Chem. , vol.50 , pp. 6366-6370
    • Khrimian, A.1    Klun, J.A.2    Hijji, Y.3    Baranchikov, Y.N.4    Pet'ko, V.M.5    Mastro, V.C.6    Kramer, M.H.7
  • 14
    • 33751392551 scopus 로고
    • A novel regio- and stereospecific hydrohalogenation reaction of 2-propynoic acid and its derivatives
    • Ma, S.; Lu, X.; Li, Z. A novel regio- and stereospecific hydrohalogenation reaction of 2-propynoic acid and its derivatives. J. Org. Chem. 1992, 57, 709-713.
    • (1992) J. Org. Chem. , vol.57 , pp. 709-713
    • Ma, S.1    Lu, X.2    Li, Z.3
  • 15
    • 0034723430 scopus 로고    scopus 로고
    • In situ manganese dioxide alcohol oxidation-Wittig reactions: Preparation of bifunctional dienyl building blocks
    • Wei, X.; Taylor, R. J. K. In situ manganese dioxide alcohol oxidation-Wittig reactions: Preparation of bifunctional dienyl building blocks. J. Org. Chem. 2000, 65, 616-620.
    • (2000) J. Org. Chem. , vol.65 , pp. 616-620
    • Wei, X.1    Taylor, R.J.K.2
  • 16
    • 85050517682 scopus 로고
    • 3. Tetrakis[Iodo(tri-n-butylphosphine)-copper(I)] and iodo-(2,2′-bipyridine)-(tri-n-butylphosphine)copper(I)
    • Kauffman, G. B.; Teter, L. A. 3. Tetrakis[Iodo(tri-n-butylphosphine)-copper(I)] and iodo-(2,2′ -bipyridine)-(tri-n-butylphosphine)copper(I). Inorg. Synth. 1963, 7, 9-12.
    • (1963) Inorg. Synth. , vol.7 , pp. 9-12
    • Kauffman, G.B.1    Teter, L.A.2
  • 17
    • 18844410382 scopus 로고
    • Catalytic asymmetric epoxidation and kinetic resolution: Modified procedure including in situ derivatization
    • Gao, Y.; Hanson, R. M.; Klunder, J. M.; Ko, S. Y.; Masamune, H.; Sharpless, K. B. Catalytic asymmetric epoxidation and kinetic resolution: Modified procedure including in situ derivatization. J. Am. Chem. Soc. 1987, 109, 5765-5780.
    • (1987) J. Am. Chem. Soc. , vol.109 , pp. 5765-5780
    • Gao, Y.1    Hanson, R.M.2    Klunder, J.M.3    Ko, S.Y.4    Masamune, H.5    Sharpless, K.B.6
  • 18
    • 0000005260 scopus 로고
    • A new route to cyclopentene-1-carboxaldehydes by rearrangement of 2,3-epoxycyclohexanols
    • Magnusson, G.; Thoren, S. A new route to cyclopentene-1-carboxaldehydes by rearrangement of 2,3-epoxycyclohexanols. J. Org. Chem. 1973, 38, 1380-1384.
    • (1973) J. Org. Chem. , vol.38 , pp. 1380-1384
    • Magnusson, G.1    Thoren, S.2
  • 19
    • 0034629333 scopus 로고    scopus 로고
    • Stereoselective synthesis of C5-C20 and C21-C34 subunits of the core structure of the aplyronines. Application of enantioselective additions of chiral allenylindium reagents to chiral aldehydes
    • Marshall, J. A.; Johns, B. A. Stereoselective synthesis of C5-C20 and C21-C34 subunits of the core structure of the aplyronines. Application of enantioselective additions of chiral allenylindium reagents to chiral aldehydes. J. Org. Chem. 2000, 65, 1501-1510.
    • (2000) J. Org. Chem. , vol.65 , pp. 1501-1510
    • Marshall, J.A.1    Johns, B.A.2
  • 20
    • 33947086247 scopus 로고
    • Catalytic hydrogenation. VI. The reaction of sodium borohydride with nickel salts in ethanol solution. P-2 Nickel, a highly convenient, new, selective hydrogenation catalyst with great sensitivity to substrate structure
    • Brown, C. A.; Ahuja, V. K. Catalytic hydrogenation. VI. The reaction of sodium borohydride with nickel salts in ethanol solution. P-2 Nickel, a highly convenient, new, selective hydrogenation catalyst with great sensitivity to substrate structure. J. Org. Chem. 1973, 38, 2226-2230.
    • (1973) J. Org. Chem. , vol.38 , pp. 2226-2230
    • Brown, C.A.1    Ahuja, V.K.2
  • 21
    • 0000922375 scopus 로고
    • Synthesis of Z,Z-skipped diene macrolide pheromones for Cryptolestes and Oryzaephilus grain beetles (Coleoptera: Cucujidae)
    • Millar, J. G.; Oehlschlager, A. C. Synthesis of Z,Z-skipped diene macrolide pheromones for Cryptolestes and Oryzaephilus grain beetles (Coleoptera: Cucujidae). J. Org. Chem. 1984, 49, 2332-2338.
    • (1984) J. Org. Chem. , vol.49 , pp. 2332-2338
    • Millar, J.G.1    Oehlschlager, A.C.2
  • 22
    • 0000587893 scopus 로고
    • Alkylative epoxide rearrangement. A stereospecific approach to chiral epoxide pheromones
    • Bell, T. W.; Ciaccio, J. A. Alkylative epoxide rearrangement. A stereospecific approach to chiral epoxide pheromones. J. Org. Chem. 1993, 58, 5153-5162.
    • (1993) J. Org. Chem. , vol.58 , pp. 5153-5162
    • Bell, T.W.1    Ciaccio, J.A.2
  • 23
    • 0029103956 scopus 로고
    • Determining enantiomeric composition of disparlure
    • Oliver, J. E.; Waters, R. M. Determining enantiomeric composition of disparlure. J. Chem. Ecol. 1995, 21, 199-211.
    • (1995) J. Chem. Ecol. , vol.21 , pp. 199-211
    • Oliver, J.E.1    Waters, R.M.2
  • 24
    • 0012815040 scopus 로고
    • The first practical method for asymmetric epoxidation
    • Sharpless, K. B.; Katsuki, T. The first practical method for asymmetric epoxidation. J. Am. Chem. Soc. 1980, 102, 5974-5976.
    • (1980) J. Am. Chem. Soc. , vol.102 , pp. 5974-5976
    • Sharpless, K.B.1    Katsuki, T.2
  • 25
    • 0026343964 scopus 로고
    • Pheromone synthesis; CXXXIII. Synthesis of both the enantiomers of (3Z,9Z)-cis-6,7-epoxy-3,9-nonadecadiene, a pheromone component of Erannis defoliaria
    • Mori, K.; Brevet, J.-L. Pheromone synthesis; CXXXIII. Synthesis of both the enantiomers of (3Z,9Z)-cis-6,7-epoxy-3,9-nonadecadiene, a pheromone component of Erannis defoliaria. Synthesis 1991, 1125-1129.
    • (1991) Synthesis , pp. 1125-1129
    • Mori, K.1    Brevet, J.-L.2
  • 26
    • 0031323668 scopus 로고    scopus 로고
    • Regioselectivity of reaction of cuprous acetylides with 1-bromo-2-butene
    • Matveeva, E. D.; Erin, A. S.; Kurz, A. L. Regioselectivity of reaction of cuprous acetylides with 1-bromo-2-butene. Russ. J. Org. Chem. 1997, 33, 1061-1064.
    • (1997) Russ. J. Org. Chem. , vol.33 , pp. 1061-1064
    • Matveeva, E.D.1    Erin, A.S.2    Kurz, A.L.3
  • 27
    • 0001172890 scopus 로고
    • Reactions r of 2,3-epoxyhalides. Synthesis of optically active allylic alcohols and homoallylic epoxides
    • Nicolaou, K. C.; Duggan, M. E.; Ladduwahetty, T. Reactions r of 2,3-epoxyhalides. Synthesis of optically active allylic alcohols and homoallylic epoxides. Tetrahedron Lett. 1984, 25, 2069-2072.
    • (1984) Tetrahedron Lett. , vol.25 , pp. 2069-2072
    • Nicolaou, K.C.1    Duggan, M.E.2    Ladduwahetty, T.3
  • 28
    • 2442536414 scopus 로고
    • Synthesis of racemic cis-3,cis-6,cis-9,10-epoxyheneicosadiene-a component of the sex pheromone of the American white butterfly Hyphantria cunea Drury
    • Nikolayeva, L. A.; Kovalev, B. G. Synthesis of racemic cis-3,cis-6,cis-9,10-epoxyheneicosadiene-a component of the sex pheromone of the American white butterfly Hyphantria cunea Drury. J. Org. Chem. USSR 1985, 21, 676-679.
    • (1985) J. Org. Chem. USSR , vol.21 , pp. 676-679
    • Nikolayeva, L.A.1    Kovalev, B.G.2
  • 29
    • 2442614402 scopus 로고
    • tri-O-Acetyl-D-galactal in the synthesis of (3Z,6Z,9S,10R)-cis-9,10-epoxy-3,6-heneicosadiene-a component of the sex pheromone of the American white butterfly (Hyphantria cunea drury (sic))
    • Tolstikov, A. G.; Khakhalina, N. V.; Spirikhin, L. V.; Khalilov, L. M.; Panasenko, A. A.; Odinokov, V. N.; Yolstikov, G. A. tri-O-Acetyl-D-galactal in the synthesis of (3Z,6Z,9S,10R)-cis-9,10-epoxy-3,6-heneicosadiene-a component of the sex pheromone of the American white butterfly (Hyphantria cunea drury (sic)). J. Org. Chem. USSR 1991, 27, 679-684.
    • (1991) J. Org. Chem. USSR , vol.27 , pp. 679-684
    • Tolstikov, A.G.1    Khakhalina, N.V.2    Spirikhin, L.V.3    Khalilov, L.M.4    Panasenko, A.A.5    Odinokov, V.N.6    Yolstikov, G.A.7
  • 30
    • 33845374483 scopus 로고
    • Synthesis of chiral bis-homoallylic epoxides. A new class of lepidopteran sex attractants
    • Millar, J. G.; Underhill, E. W. Synthesis of chiral bis-homoallylic epoxides. A new class of lepidopteran sex attractants. J. Org. Chem. 1986, 51, 4726-4728.
    • (1986) J. Org. Chem. , vol.51 , pp. 4726-4728
    • Millar, J.G.1    Underhill, E.W.2
  • 31
    • 0037395147 scopus 로고    scopus 로고
    • Synthesis of all four stereoisomers of leucomalure, components of the female sex pheromone of the satin moth, Leucoma salicis
    • Muto, S.; Mori, K. Synthesis of all four stereoisomers of leucomalure, components of the female sex pheromone of the satin moth, Leucoma salicis. Eur. J. Org. Chem. 2003, 1300-1307.
    • (2003) Eur. J. Org. Chem. , pp. 1300-1307
    • Muto, S.1    Mori, K.2
  • 32
    • 0001081376 scopus 로고
    • The carbonyl epoxide rearrangement. A chiral synthesis of the Mus musculus pheromone
    • Wasserman, H. H.; Oku, T. The carbonyl epoxide rearrangement. A chiral synthesis of the Mus musculus pheromone. Tetrahedron Lett. 1986, 27, 4913-4916.
    • (1986) Tetrahedron Lett. , vol.27 , pp. 4913-4916
    • Wasserman, H.H.1    Oku, T.2
  • 33
    • 0034742453 scopus 로고    scopus 로고
    • Synthesis of (±)-leucomalure [(3Z,6R*,7S*,9R* ,10S*)-cis-6,7-cis-9,10-diepoxy-3-henicosene], the major component of the female sex pheromone of the satin moth
    • Lizarraga, J. R.; Mori, K. Synthesis of (±)-leucomalure [(3Z,6R*,7S*,9R*,10S*)-cis-6,7-cis-9, 10-diepoxy-3-henicosene], the major component of the female sex pheromone of the satin moth. Nat. Prod. Lett. 2001, 15, 89-92.
    • (2001) Nat. Prod. Lett. , vol.15 , pp. 89-92
    • Lizarraga, J.R.1    Mori, K.2
  • 35
    • 0345400063 scopus 로고
    • New dispenser for the pheromone of the gypsy moth (Lepidoptera: Lymantriidae)
    • Leonhardt, B. A.; Mastro, V. C.; DeVilbiss, E. D. New dispenser for the pheromone of the gypsy moth (Lepidoptera: Lymantriidae). Forest Entomol. 1993, 86, 821-827.
    • (1993) Forest Entomol. , vol.86 , pp. 821-827
    • Leonhardt, B.A.1    Mastro, V.C.2    DeVilbiss, E.D.3


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