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Compound - 1S5R-frontalin [(1S,5R)-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 ]  [Behavioural function

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Reference(s) for synthesis of (1S,5R)-1,5-Dimethyl-6,8-dioxabicyclo[3.2.1]octane [1S5R-frontalin]

Chenevert, R., and Caron, D. 2002. Chemoenzymatic enantioselective synthesis of (1S,5R)-(-)-frontalin. Tetrahedron: Asymmetry. 13:339-342.
Fuganti, C., Grasselli, P., and Servi, S. 1983. Synthesis of (-)-frontalin from the (2S,3R)-diol from alpha-methylcinnamaldehyde and fermenting Baker's yeast. J. Chem. Soc. Perkin Trans. 1:241-244.
Ibrahim, N., Eggimann, T., Dixon, E.A., and Wieser, H. 1990. The absolute configuration of 6,8-dioxabicyclo[3.2.1]octane and several methyl substituted derivatives. Tetrahedron. 46:1503-1514.
Lee, A.W.M. 1983. Total synthesis of (+)- and (-)-frontalin. J. Chem. Soc. Chem. Comm. 579.
Magnus, P.O., and Roy, G. 1978. A short synthesis of (-)-(+)-frontalin and Latia luciferin using new organosilicon reagents. J. Chem. Soc. Chem. Comm. 7:297-298.
Meister, C., and Scharf, H.-D. 1983. Synthese von (+)-(-)-frontalin. Liebigs Ann. Chem. 913.
Meister, C., and Scharf, H.-D. 1983. Synthese von (1S)-(-)-frontalin. Liebigs Ann. Chem. 6:913-921.
Mori, K. 1975. Synthesis of optically active forms of frontalin: the pheromone of Dendroctonus bark beetles. Tetrahedron. 31:1381-1384.
Naef, R., and Seebach, D. 1983. Vierstufige EPC-Synthese von (+)- oder (-)-frontalin aus milchsaeure. Eine erste anwendung des prinzips der selbstreproduktion der chiralitaet in der naturstoffsynthese. Liebigs Ann. Chem. 1930-1936.
Ohrui, H., and Emoto, S. 1976. A synthesis of (S)-(-)-frontalin from D-glucose. Agric. Biol. Chem. 40:2267.
Trinh, M.-C., Florent, J.-C., and Monneret, C. 1987. Synthesis of (-)-frontalin from alpha-D-isosaccharino-1,4-lactone. J. Chem. Soc. Chem. Comm. 8:615-616.
Whiteside, J.K., and Buchanan, C.M. 1986. Synthesis of (-)- and (+)-frontalin. J. Org. Chem. 51:5443-5445.
Yus, M., Ramon, D.J., and Prieto, O. 2003. (-)-frontalin: synthesis using the catalytic enantioselective addition of dimethylzinc to a ketone. Eur. J. Org. Chem. 15:2745-2748.

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