Abstract
A new way of synthesis was developed for racemic 8-nonene-2,4-diol, the acyclic precursor of l.3-dimethyl-l,9-dioxabicyclo[3.l.l] nonane. The latter substance was isolated from the bark of an ordinary spruce affected with a pest Trypodendron Lineatum Oliv.
Similar content being viewed by others
References
Heemann, V. and Francke, W.,Naturwiss., 1976, vol. 63, no. 7, p. 344.
Heemann, V. and Francke, W.,Planta Med., 1977, vol. 32, pp. 342–343.
Vite, J.P. and Francke, W.,Naturwiss., 1976, vol. 63, pp. 550–551.
Gerlach, H. and Kunzler, P.,Helv. Chim. Acta, 1977, vol. 60, no. 2, pp. 638–642.
Vite, J.P., Heemann, V., and Francke, W.,Tetrahedron Lett., 1984, vol. 5, no. 20, pp. 2175–2176.
Mohr, P. and Tamm, C.,Tetrahedron Lett., 1987, vol. 28, no. 4, pp. 395–396.
Adams, J. and Frenette, R.,Tetrahedron Lett., 1987, vol. 28, no. 41, pp. 4773–4774.
Bulmon Page, P.C., Rayner, C.M., and Sutherland, J.O.,Tetrahedron Lett., 1986, vol. 27, no. 30, pp. 3535–3538.
Guindon, J., Denis, J.S., and Daigneault, S.,Tetrahedron Lett., 1986, vol. 27, no. 11, pp. 1237–1240.
Mori, Y., Kuharo, M., Takeuchi, A., and Suzuki, M.,Tetrahedron Lett., 1988, vol. 29, no. 42, pp. 5419–5422.
Redlich, H., Schneider, B., and Francke, W.,Tetrahedron Lett., 1980, vol. 21, no. 31, pp. 3009–3012.
Sato, T., Itoh, T., Hattori, C., and Fujisawa, T.,Chem. Lett., 1983, no. 9, pp. 1391–1392.
Bernardi, R. and Ghiringhelli, D.,J. Org. Chem., 1987, vol. 52, no. 23, pp. 5201–5202.
Redlich, H. and Schneider, B.,Liebig Ann. Chem., 1983, no. 3, pp. 393–411.
Funk, R.L. and Bolton, G.L.,Tetrahedron Lett., 1988, vol. 29, no. 10, pp. 1111–1114.
Nakata, T., Nagao, S., Takao, S., Tanaka, T., and Oishi, T.,Tetrahedron Lett., 1985, vol. 26, no. 1, pp. 75–78.
Andrus, D.W.,Org. Synth., 1943, vol. 23, p. 67.
Mori, K. and Seu, Y.B.,Tetrahedron, 1985, vol. 41, no. 16, pp. 3429–3431.
Curran, D.P. and Heffner, T.A.,J. Org. Chem., 1990, vol. 55, no. 15, pp. 4585–4595.
Mori, K., Suguro, T., and Uchido, M.,Tetrahedron, 1978, vol. 34, no. 20, pp. 3119–3123.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Vakhidov, R.R., Shakhmaev, R.N., Ishmuratov, G.Y. et al. Synthesis of racemic 8-nonene-2,4-diol, acyclic precursor of 1,3-dimethyl-1,9-dioxabicyclo[3.1.1]nonane. Russ J Electrochem 36, 771–773 (2000). https://doi.org/10.1007/BF02757428
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF02757428