Reference(s) for synthesis of exo-7-Ethyl-5-methyl-6,8-dioxabicyclo[3.2.1]octane [exo-brevicomin]
Asami, M., and Mukaiyama, T. 1983. An asymmetric synthesis of alpha-benzyloxy aldehydes having a chiral tertiary center - an application to the asymmetric synthesis of exo (+)-brevicomin. Chem. Lett. 93. |
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Bellas, T.E., Brownlee, R.G., and Silverstein, R.M. 1969. Synthesis of brevicomin, principal sex attractant in the frass of the female western pine beetle, Tetrahedron. 25:5149-5153. |
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Bernardi, R., Fuganti, C., and Grasselli, P. 1981. On the steric course of addition of Grignard reagents onto alpha-dialkoxy erythro and threo chiral aldehydes. Synthesis of (+) and (-)-exo and endo-brevicomin. Tetrahedron Lett. 22:4021-4024. |
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Brimacombe, J.S., Ferrier, R.J., 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. |
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Cahiez, G., Alexakis, A., and Normant, J.F. 1980 Simple stereospecific synthesis of the insect sex pheromones of Cossus cossus, Eupoecilia ambiguella and Orgyia pseudotsugata. Tetrahedron Lett. 21:1433-1436. |
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Chaquin, P., Morizur, J.-P., and Kossanyi, J. 1977. An easy access to exo-brevicomin. J. Am. Chem. Soc. 99:903-905. |
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Cohen, T., and Matz, J.R. 1980. A general preparative method for a-lithioethers and its application to a concise, practical synthesis of brevicomin. J. Am. Chem. Soc. 102:6900-6902. |
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Coke, J.L., Williams, H.J., and Natarajan, S. 1977. A new preparation of acetylenic ketones and application to the synthesis of exo-brevicomin, the pheromone from Dendroctonus brevicomis. J. Org. Chem. 42:2380-2382. |
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Ferrier, R.J., and Prasit, P. 1983. Unsaturated carbohydrates, Part 25. Abbreviated synthesis of the insect pheromone (+)exo-brevicomin from a nona-3,8-dienulose derivative. J. Chem. Soc. Perkin Trans. 1:1645-1647. |
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Ferrier, R.J., Schmidt, P., and Tyler, P.C. 1985. Unsaturated carbohydrates. XXVII. Synthesis of (-)-exo-brevicomin from a nona-3,8-dienulose derivative. J. Chem. Soc. Perkin Trans. 1:301-303. |
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Fuganti, C., Grasselli, P., Pedrocchi-Fantoni, G., Servi, S., and Zirotti, C. 1983. Carbohydrate-like chiral synthons. Preparatation of (R) gamma-hexanolide, (5R,6S,7S)-6,7-isopropylidendioxy-delta-octanolide and (+)-exo-brevicomin from (2S,3S,4R)-iso-propylidendioxy-4-benzyloxyhept-6-ene. Tetrahedron Lett. 24:3753-3756. |
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Giese, D., Bartmann, D., and Hasskerl, T. 1987. Synthesis of pheromones with acetal structures via C-C bond formation. Liebigs Ann. Chem. 427. |
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Gore, W.E., Pearce, G.T., and Silverstein, R.M. 1976. Mass spectrometric studies of the dioxabicyclo[3.2.1]octanes multistriatin, frontalin, and brevicomin. J. Org. Chem. 41:607-610. |
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Hatakeyama, S., Sakurai, K., and Takano, S. 1985. Preparation of (2R,3S)-1,2-epoxypent-4-en-3-ol, a new chiral building block for the synthesis of (+)-endo- and (-)-exo-brevicomin. J. Chem. Soc. Chem. Comm. 4:1759-1761. |
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Johnston, B.D., and Oehlschlager, A.C. 1982. Facile synthesis of the enantiomers of exo-brevicomin. J. Org. Chem. 47:5384-5386. |
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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. |
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Kocienski, P.J., and Ostrow, R.W. 1976. A stereoselective total synthesis of exo- and endo-brevicomin. J. Org Chem. 41:398. |
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Kuefner, U. and Schmidt, R.R. 1985. A short synthesis of d,l-exo-brevicomin from divinylglycol. Synthesis. 11:1060-1061. |
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Larcheveque, M., and Laland, J. 1985. Highly stereoselective preparation of enantiomerically pure 1,2-diols: synthesis of (+)-exobrevicomin. J. Chem. Soc. Chem. Comm. 2:83-84. |
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Lipkowitz, K.B., Mundy, B.P., and Geeseman, D. 1973. Studies directed towards a practical synthsis of brevicomins. II. A novel synthesis of 1,5-dimethyl-8-oxobicyclo[3.2.1]octane-6-one. Synth. Comm. 3:453. |
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Lipkowitz, K.B., Mundy, B.P., and Matsko, T.H. 1976. Studies directed toward a practical synthesis of brevicomin. IV. Formation and hydrogenolysis of 5,7-dimethyl-6,8-dioxabicyclo[3.2.1]octane under catalytic hydrogenation conditions. J. Org. Chem. 41:371-373. |
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Lipkowitz, K.B., Scarpone, S., Mundy, B.P., and Bornmann, W.G. 1979. Formation and synthetic utility of dihydro- and dihydrothiapyrans. J. Org. Chem. 44:486-494. |
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Masaki, Y., Nagata, K., Serizawa, Y., and Kaji, K. 1982. Short-step synthesis of optically and biologically active exo-brevicomin. Tetrahedron Lett. 23:5553-5554. |
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Matteson, D.S., and Sadhju, K.M. 1983. Boronic ester homologation with 99% chiral selectivity and its use in syntheses of the insect pheromones (3S,4S)-4-methyl-3-heptanol and exo-brevicomin. J. Amer. Chem. Soc. 105:2077-2078. |
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Matteson, D.S., Sadhu, K.M., and Peterson, M.L. 1986. 99% Chirally selective syntheses via Pinanediol boronic esters: insect pheromones, diols, and an amino acid. J. Am. Chem. Soc. 108:810-819. |
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Mayer, S.F., Mang, H., Steinreiber, A., Saf, R., and Faber, K. 2002. Asymmetric total synthesis of (+)-exo-brevicomin based on enantioconvergent biocatalytic hydrolysis of an alkene-functionalized 2,3-disubstituted epoxide. Can. J. Chem. 80:362-369. |
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Meyer, H.H. 1977. Synthese von (-)-(1S,7S)-exo-brevicomin aus (+)-(2R,3R)-weinsaeure-diethylester. Liebigs Ann. Chem. 732. |
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Mori, K., and Seu, Y.-B. 1986. Pheromone synthesis. LXXXI. New synthesis of the enantiomers of exo-brevicomin, the pheromone of Dendroctonus brevicomis Le Conte. Liebigs Ann. Chem. 205. |
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Mulzer, J., Angermann, A., and Muench, W. 1986. Enantio- and diastereocontrolled synthesis of chiral 1,2-diol derivatives from (R)-2,3-di-O-isopropylidene-glyceraldehyde, endo- and exo-brevicomin. Liebigs Ann. Chem. 825. |
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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-dioxabicyclo[3.2.1]octane. J. Org. Chem. 43:2347-2350. |
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Mundy, B.P., Lipkowitz, K.B., and Dirks, G.W. 1975. Studies directed towards a practical synthesis of brevicomin. III. Cyclization routes to 6,8-dioxabicyclo[3.2.1]octane. Synth. Comm. 5:7. |
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Mundy, B.P., Otzenberger, R.D., and De Barnardis, A.R. 1971. A synthesis of frontalin and brevicomin. J. Org. Chem. 36:2390-2390. |
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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. Magnetic Res. 27:497. |
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Rodin, J.O., Reece, C.A., Silverstein, R.M., Brown, V.H., and Degraw, J.I. 1971. Synthesis of brevicomin, principal sex attractant of Western pine beetle. J. Chem. Eng. Data. 380-381. |
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Rossi, R., and Carpita, A. 1986. Diastereoselective synthesis of (E)-alkenes and (E)- 1 ,omega-dienes starting from diastereoisomeric mixtures of 1-bromo-1-alkenes: new syntheses of monounsaturated or bridged ring-ketal naturally occurring substances. Tetrahedron Lett. 27:2529-2532. |
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Sato, T., Oikawa, T., and Kobayashi, K. 1985. Metal-catalyzed organic photoreactions. Iron(III) chloride catalyzed photooxidation of cyclic olefins and its application to the synthesis of exo-brevicomin. J. Org. Chem. 50:1646-1651. |
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Serbryakov, E.P., Gamalevich, G.D., and Shekhtman, R.I. 1985. Pheromones of Coleoptera. I. Simple synthesis of exo- and endo-brevicomins using oxy-cope rearrangement. Izv. Akad. Nauk. SSSR. Ser. Khim. 1887. |
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Seu, Y.B., and Mori, K. 1986. A new synthesis of (-)-exo-brevicomin. Agric. Biol. Chem. 50:2923. |
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Sherk, A.E., and Fraser-Reid, B. 1982. Synthetic routes to 6,8-dioxabicyclo[3 2.1]octyl pheromones from D-glucose derivatives. II. Synthecis of (+)-exo-brevicomin. J. Org. Chem. 47:932-935. |
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Silverstein, R.M. 1968. Spectrometric identification of insect sex attractants. J. Chem. Educ. 45:794. |
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Silverstein, R.M., Brownlee, R.G., Bellas, T.E., Wood, D.L., and Browne, L.E. 1968. brevicomin: principal sex attractant in the frass of the female Western pine beetle. Science. 159:889. |
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Sum, P.-E., and Weiler, L. 1979. Synthesis of exo- and endo-brevicomin and frontalin. Can. J. Chem. 57:1475. |
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Utimoto, K. 1983. Palladium catalyzed synthesis of heterocycles. Pure Appl. Chem. 55:1845. |
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Wasserman, H.H., and Barber, E.H. 1969. Carbonyl epoxide rearrangements. Synthesis of brevicomin and related [3.2.1] bicyclic systems. J. Am. Chem. Soc. 91:3674-3675. |
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Williams, H.J., Jr. 1977. I. Preparation of pheromones through cleavage reactions of ß-halo-alpha,ß-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. |
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Wuts, P.G.M., and Bigelow, S.S. 1982. A stereoselective synthesis of (±) exobrevicomin; synthetic applications of gamma-alkoxy allylboronates. Synth. Comm. 12:779. |
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Yadav, J.S., Vidyasagar, V., and Reddy, P.S. 1986. Enantiospecific synthesis of (+)-exo-brevicomin from D-xylose. Carbohydrate Res. 156:236-240.
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Yimenu, T. 1983. Synthesis of insect sex pheromones using organosilicon compounds. J. Natl. Tech. Assoc. 57:42. |
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Yusufoglu, A., Antons, S., and Scharf, H.-D. 1986. Syntheses of pure enantiomers of erythro-1,2,3-pentanetriol and their l-bromo-and 1-tosyloxy derivatives. Liebigs Ann. Chem. 1119. |
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