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Compound - frontalin [1,5-Dimethyl-6,8-dioxabicyclo[3.2.1]octane]

Bedoukain RussellIPM
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Formula: C8H14O2 
CAS#: 28401-39-0 
MW: 142.2 

[MS]  [ NMR ]  [ Kovats ]  [Behavioural function

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Reference(s) for synthesis of 1,5-Dimethyl-6,8-dioxabicyclo[3.2.1]octane [frontalin]

Bartlett, P.A., Marlowe, C.K., Connolly, P.J., Banks, K.M., Chui, W.-H., Dahlberg, P.S., Haberman, A.M., Kim, J.S., Klassen, K.J., Lee, R.W., Lum, R.T., Mebane, E.W., Ng, J.A., Ong, J.-C., Sagheb, N., Smith, B., and Yu, P. 1984. Synthesis of frontalin, the aggregation pheromone of the Southern pine beetle. J. Chem. Ed. 61:816.
Brimacombe, J.S., Ferrier, J.H., Williams, J M., and Williams, N.R. 1979. The synthesis of optically active noncarbohydrate compounds, in Specialist Periodical Reports Carbohydrate Chemistry. Vol. 11. A Review of the Literature Published During 1977, Brimacombe, J.S., Ed., The Chemical Society, London. 228.
D'Silva, T.D.J., and Peck, D.W. 1972. Convenient synthesis of frontalin - 1,5-dimethyl-6,8-dioxabicyclo[3.2.1]octane. J. Org. Chem. 37:1828-1829.
Gore, W.E., Pearce, G.T., and Silverstein, R.M. 1976. Mass spectrometric studies of the dioxabicylclo[3.2.1]octanes multistriatin, frontalin, and brevicomin. J. Org. Chem. 41:607-610.
Hagiwara, H. and Uda, H. 1985. A facile synthesis of 5-methyl-6,8-dioxabiclo[3.2.1]octan-3-ones from 4-(t-butyldimethylsiloxy)pent-3-en-2-one and protected alpha-ketols. A synthesis of ()-frontalin. J. Chem. Soc. Perkin Trans. 1:283-287.
Hicks, D.R., and Fraser-Reid, B. 1976. Synthesis of one enantiomer, the other enantiomer, and a mixture of both enantiomers of frontalin from a derivative of methyl-alpha-D-glucopyranoside. J. Chem. Soc. Chem. Comm. 21:869-870.
Jarosz, S., Hicks, D.R., and Fraser-Reid, B. 1982. Synthetic routes to 6,8-dioxabicyclo[3.2.1]octyl pheromones from D-glucose derivatives. III. Synthesis of (-)-frontalin. J. Org. Chem. 47:935-940.
Johnston, B.D., and Oehlschlager, A.C. 1984. Facile synthesis of the enantiomers of frontalin. Can. J. Chem. 62:2148.
Kinzer, G.W., Fentiman, A.F., Jr., Page, T.F., Jr., Foltz, L., Vite, J.P., and Pitman, G.P. 1969. Bark beetle attractants: identification, synthesis and field bioassay of a new compound isolated from Dendroctonus. Nature. 221:477.
Kongkathip, B., Sookkho, R., and Kongkathip, N. 1985. Convenient synthetic route to (+)-frontalin. Chem. Lett. 1849.
Mori, K., Kobayashi, S., and Matsui, M. 1975. A synthesis of ()-frontalin, the pheromone of Dendroctonus bark beetles. Agric. Biol. Chem. 39:1889.
Mundy, B.P., Dirks, G.W., Larsen, R.D., and Caughlan, C.D. 1978. Synthesis and molecular structure of exo-7-phenyl-5,7-dimethyl-6,8-dioxahicyclo[3.2.1]octane. J. Org. Chem. 43:2347-2350.
Mundy, B.P., Otzenberger, R.D., and De Barnardis, A.R. 1971. A synthesis of frontalin and brevicomin. J. Org. Chem. 36:2390-2390.
Pearce, G.T, Gore, W.E., and Silverstein, R.M. 1977. Carbon-13 spectra of some insect pheromones and related compounds of the 6-8-dioxabicyclo[3.2.1]octane system. J. Mag. Res. 27:497.
Sakito, Y., and Mukaiyama, T. 1979. Asymmetric synthesis of two enantiomers of frontalin. Chem. Lett. 1027.
Sato, T., Kaneko, H., and Yamaguchi, S. 1980. Metal-catalyzed organic photoreactions. Titanium (IV) chloride catalyzed photoreaction of saturated ketones with methanol and its application to the synthesis of frontalin. J. Org. Chem. 45:3778-3782.
Sato, T., Yamaguchi, S., and Kaneko, H. 1979. Metal-catalyzed organic photoreactions. One-step synthesis of ()-frontalin by the titanium (IV) chloride-catalyzed photoreaction of heptane-2,6-dione. Tetrahedron Lett. 21:1863-1864.
Serebryakov, E.P., and Gamalevich, G.D. 1985. Pheromones of Coleoptera. II. Simple synthesis of (+)-frontalin using low-temperature oxy-cope rearrangement. Izv. Akad. Nauk. SSSR. Ser. Khim. 1890.
Sum, P.-E., and Weiler, L. 1979. Synthesis of exo- and endo-brevicomin and frontalin. Can. J. Chem. 57:1475.
Trehan, I.R., Kad, G.L., and Gupta, S. 1986. A new synthesis of (+)-frontalin, the pheromone of Dendroctonus bark beetles. Ind. J. Chem. 25B:1243-1244.
Utaka, M., Makino, H., Oota, Y., Tsuboi, S., and Takeda, A. 1983. Facile preparation of 2,6-dimethyl-2,6-tetrahydropyrancarbolactone, a versatile intermediate for the syntheses of ()-frontalin, ()-cinenic acid, and ()-linaloyl oxide. Tetrahedron Lett. 24:2567-2570.
Utimoto, K. 1983. Palladium catalyzed synthesis of heterocycles. Pure Appl. Chem. 55:1845.
Williams, H.J., Jr. 1977. I. Preparation of pheromones through cleavage reactions of beta-halo-alpha, beta-unsaturated ketones. II. Preparation of pheromones and pheromone analogues using other methods. III. Preparation of optically active alpha-methylene-gamma-lactones, Ph. D. thesis, University of North Carolina, Raleigh, NC.
Wilson, R.M., and Rekers, J.W. 1981. Decomposition of bicyclic endoperoxides: an isomorphous synthesis of frontalin via 1,5-dimethyl-6,7-dioxabicyclo[3.2.1]octane. J. Am. Chem. Soc. 103:206-207.

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