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Compound - exo-brevicomin


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Formula: C9H16O2 
CAS#: 62255-25-8 
MW: 156.22 

[MS]  [Behavioural function]  [Chemdraw

Dots surface:

Reference(s) for synthesis of exo-7-Ethyl-5-methyl-6,8-dioxabicyclo[3.2.1]octane

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.
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.
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.
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.
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.
Chaquin, P., Morizur, J.-P., and Kossanyi, J. 1977. An easy access to exo-brevicomin. J. Am. Chem. Soc. 99:903-905.
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.
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.
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.
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.
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.
Giese, D., Bartmann, D., and Hasskerl, T. 1987. Synthesis of pheromones with acetal structures via C-C bond formation. Liebigs Ann. Chem. 427.
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.
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.
Johnston, B.D., and Oehlschlager, A.C. 1982. Facile synthesis of the enantiomers of exo-brevicomin. J. Org. Chem. 47:5384-5386.
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.
Kocienski, P.J., and Ostrow, R.W. 1976. A stereoselective total synthesis of exo- and endo-brevicomin. J. Org Chem. 41:398.
Kuefner, U. and Schmidt, R.R. 1985. A short synthesis of d,l-exo-brevicomin from divinylglycol. Synthesis. 11:1060-1061.
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.
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.
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.
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.
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.
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.
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.
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.
Meyer, H.H. 1977. Synthese von (-)-(1S,7S)-exo-brevicomin aus (+)-(2R,3R)-weinsaeure-diethylester. Liebigs Ann. Chem. 732.
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.
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.
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.
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.
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. Magnetic Res. 27:497.
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.
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.
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.
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.
Seu, Y.B., and Mori, K. 1986. A new synthesis of (-)-exo-brevicomin. Agric. Biol. Chem. 50:2923.
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.
Silverstein, R.M. 1968. Spectrometric identification of insect sex attractants. J. Chem. Educ. 45:794.
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.
Sum, P.-E., and Weiler, L. 1979. Synthesis of exo- and endo-brevicomin and frontalin. Can. J. Chem. 57:1475.
Utimoto, K. 1983. Palladium catalyzed synthesis of heterocycles. Pure Appl. Chem. 55:1845.
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.
Williams, H.J., Jr. 1977. I. Preparation of pheromones through cleavage reactions of -halo-alpha,-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.
Wuts, P.G.M., and Bigelow, S.S. 1982. A stereoselective synthesis of () exobrevicomin; synthetic applications of gamma-alkoxy allylboronates. Synth. Comm. 12:779.
Yadav, J.S., Vidyasagar, V., and Reddy, P.S. 1986. Enantiospecific synthesis of (+)-exo-brevicomin from D-xylose. Carbohydrate Res. 156:236-240. .
Yimenu, T. 1983. Synthesis of insect sex pheromones using organosilicon compounds. J. Natl. Tech. Assoc. 57:42.
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.

Citation: El-Sayed AM 2018. The Pherobase: Database of Pheromones and Semiochemicals. <>.
2003-2018 The Pherobase - Extensive Database of Pheromones and Semiochemicals. Ashraf M. El-Sayed.
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