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Synthesis of racemic 8-nonene-2,4-diol, acyclic precursor of 1,3-dimethyl-1,9-dioxabicyclo[3.1.1]nonane

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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.

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References

  1. Heemann, V. and Francke, W.,Naturwiss., 1976, vol. 63, no. 7, p. 344.

    Article  CAS  Google Scholar 

  2. Heemann, V. and Francke, W.,Planta Med., 1977, vol. 32, pp. 342–343.

    Article  CAS  Google Scholar 

  3. Vite, J.P. and Francke, W.,Naturwiss., 1976, vol. 63, pp. 550–551.

    Article  CAS  Google Scholar 

  4. Gerlach, H. and Kunzler, P.,Helv. Chim. Acta, 1977, vol. 60, no. 2, pp. 638–642.

    Article  CAS  Google Scholar 

  5. Vite, J.P., Heemann, V., and Francke, W.,Tetrahedron Lett., 1984, vol. 5, no. 20, pp. 2175–2176.

    Google Scholar 

  6. Mohr, P. and Tamm, C.,Tetrahedron Lett., 1987, vol. 28, no. 4, pp. 395–396.

    Article  CAS  Google Scholar 

  7. Adams, J. and Frenette, R.,Tetrahedron Lett., 1987, vol. 28, no. 41, pp. 4773–4774.

    Article  CAS  Google Scholar 

  8. Bulmon Page, P.C., Rayner, C.M., and Sutherland, J.O.,Tetrahedron Lett., 1986, vol. 27, no. 30, pp. 3535–3538.

    Article  Google Scholar 

  9. Guindon, J., Denis, J.S., and Daigneault, S.,Tetrahedron Lett., 1986, vol. 27, no. 11, pp. 1237–1240.

    Article  CAS  Google Scholar 

  10. Mori, Y., Kuharo, M., Takeuchi, A., and Suzuki, M.,Tetrahedron Lett., 1988, vol. 29, no. 42, pp. 5419–5422.

    Article  CAS  Google Scholar 

  11. Redlich, H., Schneider, B., and Francke, W.,Tetrahedron Lett., 1980, vol. 21, no. 31, pp. 3009–3012.

    Article  CAS  Google Scholar 

  12. Sato, T., Itoh, T., Hattori, C., and Fujisawa, T.,Chem. Lett., 1983, no. 9, pp. 1391–1392.

  13. Bernardi, R. and Ghiringhelli, D.,J. Org. Chem., 1987, vol. 52, no. 23, pp. 5201–5202.

    Google Scholar 

  14. Redlich, H. and Schneider, B.,Liebig Ann. Chem., 1983, no. 3, pp. 393–411.

  15. Funk, R.L. and Bolton, G.L.,Tetrahedron Lett., 1988, vol. 29, no. 10, pp. 1111–1114.

    Article  CAS  Google Scholar 

  16. Nakata, T., Nagao, S., Takao, S., Tanaka, T., and Oishi, T.,Tetrahedron Lett., 1985, vol. 26, no. 1, pp. 75–78.

    Article  CAS  Google Scholar 

  17. Andrus, D.W.,Org. Synth., 1943, vol. 23, p. 67.

    CAS  Google Scholar 

  18. Mori, K. and Seu, Y.B.,Tetrahedron, 1985, vol. 41, no. 16, pp. 3429–3431.

    Article  CAS  Google Scholar 

  19. Curran, D.P. and Heffner, T.A.,J. Org. Chem., 1990, vol. 55, no. 15, pp. 4585–4595.

    Article  CAS  Google Scholar 

  20. Mori, K., Suguro, T., and Uchido, M.,Tetrahedron, 1978, vol. 34, no. 20, pp. 3119–3123.

    Article  CAS  Google Scholar 

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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

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  • DOI: https://doi.org/10.1007/BF02757428

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