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Compound - olean

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

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Reference(s) for synthesis of 1,7-Dioxaspiro[5.5]undecane 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.