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Compound - alpha-multistriatin [2,4-Dimethyl-5-ethyl-6,8-dioxabicyclo[3.2.1]octane]

Bedoukain RussellIPM
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Formula: C10H18O2 
CAS#: 59014-03-8 
MW: 170.25 

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

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Reference(s) for synthesis of 2,4-Dimethyl-5-ethyl-6,8-dioxabicyclo[3.2.1]octane [alpha-multistriatin]

Bartlett, P.A., and Myerson, J. 1979. Highly stereoselective synthesis of (+)-alpha-multistriatin. J. Org. Chem. 44:1625-1627.
Beck, K. 1978. Pheromone chemistry of the smaller European elm bark beetle. J. Chem. Ed. 55:567.
Elliot, W.J., and Fried, J. 1976. Stereocontrolled synthesis of alpha-multistriatin, an essential component of the aggregation pheromone for the European elm bark beetle. J. Org. Chem. 41:2475-2476.
Elliott, W.J., Hromnak, G., Fried, J., and Lanier, G.N. 1979. Synthesis of multistriatin enantiomers and their action on Scolytus multistriatus (Coleoptera: Scolytidae). J. Chem. Ecol. 5:279-287.
Gore, W.E., and Armitage, I.M. 1976. Lanthanide-induced chemical shifts and the relative stereochemistry of multistriatin (2,4-dimethyl-5-ethyl-6,8-dioxabicyclo[3.2.1] octane). J. Org. Chem. 41:1926-1930.
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.
Helbig, W. 1984. Stereoselektive Synthese von Alkoholen. XVII. Stereoselektive Synthese von optisch aktivem alpha-multistriatin, einem lockstoff des kleinen Europaeischen ulmensplintkaefers, Scolytus multistriatus. Liebigs Ann. Chem. 1165.
Hoffmann, R.W., and Helbig, W. 1981. Stereoselektive Synthese von Alkoholen, X. Diastereoselektive Synthese von (-)-delta-multistriatin. Chem. Ber. 114:2802.
Joshi, N.N., Mamdapur, V.R., and Chadha, M,S. 1983. Convenient synthetic route to 6,8-dioxabicyclo[3.2.1]octanes, the aggregation pheromone components of bark beetles. J. Chem. Soc. Perkin Trans. 1:2963-2966.
Lanier, G.N., Gore, W.E., Pearce, G.T., Peacock, J.W., and Silverstein, R.M. 1977. Response of the European elm bark beetle, Scolytus multistriatus (Coleoptera: Scolytidae), to isomers and components of its pheromone. J. Chem. Ecol. 3:1-8.
Lanier, G.N., Silverstein, R.M., and Peacock, J.W. 1976. Attractant pheromone of the European elm bark beetle (Scolytus multistriatus) isolation, identification, synthesis, and utilization studies, in Perspectives in Forest Entomology, Anderson, J. F. and Kaya, H. K., Eds., Academic Press, N. Y.149.
Marino, J.P., and Abe, H. 1981. Stereospecific 1,4-additions of methyl cyanocuprate to enol phosphates of alpha,-epoxycyclohexanones: application to the total synthesis of ()-alpha-multistriatin. J. Org. Chem. 46:5379-5383.
Mori, K., and Iwasawa, H. 1980. Stereoselective synthesis of optically active forms of delta-multistriatin, the attractant for European populations of the smaller European elm bark beetle. Tetrahedron. 36:87-90.
Mulzer, J., de Lasalle, P., and Freissler, A. 1986. Addition of crotylchromium (II) and dilithium propionate to (R)-2,3-O-isopropylideneglyceraldehyde: steric course and synthetic application in a formal synthesis of (+)- and (-)-delta-multistriatin. Liebigs Ann. Chem. 1152.
Peacock, J.W., Cuthbert, R.A., Gore, W.E., Lanier, G.N., Pearce, G.T., and Silverstein, R.M. 1975. Collection on Porapak Q of the aggregation pheromone of Scolytus multistriatus (Coleoptera: Scolytidae). J. Chem. Ecol. 1:149.
Pearce, G.T., Gore, W.E., and Silverstein, R.M. 1976. Synthesis and absolute configuration of multistriatin. J. Org. Chem. 41:2797-2803.
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.
Pearce, G.T., Gore, W.E., Silverstein, R.M., Peacock, J.W., Cuthbert, R.A., Lanier, G.N., and Simeone, J.B. 1975. Chemical attractants for the smaller European elm bark beetle Scolytus multistriatus (Coleoptera: Scolytidae). J. Chem. Ecol. 1:115-124.
Plaumann, D.E., Fitzsimmons, B.J., Ritchie, B.M., and Fraser-Reid, B. 1982. Synthetic routes to 6,8-dioxabicyclo[3.2.1]octyl pheromones from D-glucose derivatives. IV. Synthesis of (-)-alpha-multistriatin. J. Org. Chem. 47:941-946.

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