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Compound - endo-brevicomin


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Formula: C9H16O2 
CAS#: 62532-53-0 
MW: 156.22 

[MS]  [Behavioural function]  [Chemdraw

Dots surface:

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

Bellas, T.E., Brownlee, R.G., and Silverstein, R.M. 1969. Synthesis of brevicomin, principal sex attractant in the frass of the female Westem 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.
Byrom, N.T., Grigg, R., and Kongkathip, B. 1976. Catalytic synthesis of endo-brevicomin and related di- and tri-oxabicyclo[x.2.1]systems. J. Chem. Soc. Chem. Comm. 6:216-217.
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.
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. 24:1759-1761.
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.
Knolle, J., and Schäfer, H.J. 1975. Synthesis of brevicomin by kolbe electrolysis. Angew. Chem. Int. Ed. Engl. 14:758-758.
Kocienski, P.J., and Ostrow, R.W. 1976. A stereoselective total synthesis of exo- and endo-brevicomin. J. Org. Chem. 41:398-400.
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.
Look, M. 1976. Improved synthesis of endo-brevicomin for the control of bark beetles. J. Chem. Ecol. 2:83-86.
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.
Mori, K. 1974. Synthesis of exo-brevicomin, the pheromone of Western pine beetle, to obtain optically active forms of known absolute configuration. Tetrahedron. 30:4223-4227.
Mori, K. 1976. A stereoselective synthesis of (±)-endo-brevicomin, a pheromone inhibitor produced by Dendroctonus bark beetles. Agric. Biol. Chem. 40:2499.
Mori, K., and Seu, Y.-R. 1985. Synthesis of both the enantiomers of endo-brevicomin. the aggregation pheromone of Dryocoetes autographus. Tetrahedron. 41:3429-3431.
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., 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.
Oehlschlager, A.C., and Johnston, B.D. 1987. Synthesis of the enantiomers of endo-brevicomin. J. Org. Chem. 52:940-943.
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. 16:380-381.
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.
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.
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 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.
Wuts, P.G.M., and Bigelow, S.S. 1982. A stereoselective synthesis of (±)-exobrevicomin; synthetic applications of gamma-alkoxy allylboronates. Synth. Comm. 12:779.
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 1-bromo-and 1-tosyloxy derivatives. Liebigs Ann. Chem. 1119.
Yusufoglu. A., Antons, S., and Scharf, H.-D. 1986. Enantioselective synthesis and absolute configuration of both enantiomers of endo-brevicomin. J. Org. Chem. 51:3485-3487.

Citation: El-Sayed AM 2014. The Pherobase: Database of Insect Pheromones and Semiochemicals. <>.
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