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Compound - olean [1,7-Dioxaspiro[5.5]undecane]

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1,7-Dioxaspiro[5.5]undecane Formula:  C9H16O2  CAS#:  180-84-7  MW:  156.22  [MS]  [ NMR ]  [Behavioural function]

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Reference(s) for synthesis of 1,7-Dioxaspiro[5.5]undecane [olean] Baker, R., Herbert, R., Howse, P.E., Jones, O.T., Francke, W., and Reith, W. 1980. Identification and synthesis of the major sex pheromone of the olive fly (Dacus oleae). J. Chem. Soc. Chem. Comm. 2:52-53.   Chan, J.Y.C., Hough, L., and Richardson, A.C. 1985. The synthesis of (R)- and (S)-spirobi-1,4-dioxane and related spirobicycles from D-fructose. J. Chem. Soc. Perkin Trans. 1:1457-1462.   Fletcher, M.T., Mazomenos, B.E., Georgakopoulos, J.H., Konstantopoulou, M.A., Wood, B.J., De Voss, J.J., and Kitching, W. 2002. Sex pheromone biosynthesis in the female olive fruit-fly. Double labelling from [(18)O2]-dioxygen into 1,7-dioxaspiro[5.5]undecane. Chem. Comm. 12:1302-1303.   Ley, S.V. and Lygo, B. 1984. A new route to spiro-ketals using the Horner-Wittig reaction of 2-diphenyl-phosphinoxy cyclic ethers. Tetrahedron Lett. 25:113-116.   Ley, S.V., Lygo, B., Sternfeld, F., and Wonnacott, A. 1986. Alkylation reactions of anions derived from 2-benzenesulphonyl tetrahydropyran and their application to spiroketal synthesis. Tetrahedron. 42:4333-4342.   Mori, D., Uematsu, T., Yanagi, K., and Minobe, M. 1985. Synthesis of the optically active forms of 4,10-dihydroxy-1,7-dioxaspiro[5.5]undecane and their conversion to the enantiomers of 1,7-dioxaspiro[5.5]undecane, the olive fly pheromone. Tetrahedron. 41:2751-2758.   Mori, K., Uematsu, T., Watanabe, H., Yanagi, K., and Minobe, M. 1984. Synthesis of the enantiomers of 1,7-dioxaspiro[5.5]undecane and 4-hydroxy-1,7-dioxaspiro[5.5]undecane, the components of the olive fly pheromone. Tetrahedron Lett. 25:3875-3878.   Neokosmidi, A., Ragoussis, V., Zikos, C., Paravatou Petsotas, M., Livaniou, E., Ragoussis, N., and Evangelatos, G. 2004. Synthesis of haptens and development of an immunoassay for the olive fruit fly pheromone. J. Agric. Food Chem. 52:4368-4374.   Reddy, G.B., and Mitra, R.B. 1986. Acetone dimethyl hydrazone: useful synthon for the synthesis of pheromones with keto and spiro ketal functions. Synth. Comm. 16:1723.   Redlich, H., and Francke, W. 1984. Synthesis of enantiomerically pure 1,7-dioxaspiro[5.5]undecanes, pheromone components of the olive fly (Dacus oleae). Angew. Chem. Int. Ed. Engl. 23:519-520.