Synthesis of (±)-trans-cyclohexa-3,5-diene-1,2-diol derivatives from myo-inositol

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Hari Babu Mereyala and Madhavi Pannala


Abstract

myo-Inositol 8 has been converted to biscyclohexylidene ketals 9–11. The inseparable mixture of isomers 9 and 11 has been utilised as such to obtain the synthetically useful (±)-trans-cyclohexa-3,5-diene-1,2-diol derivative 24 via the intermediates 14 and 15. The trans-diol derivative 24 has also been converted to synthetically useful epoxide derivative 25 in high yield and selectivity.


References

  1. K. Stormer, Zentralbl. Bakteriol. Parasitenk. Infek., 1908, 20, 282 Search PubMed.
  2. N. L. Sohngen, Centr. Bakteriol. Parasitenk. Abt. II., 1913, 37, 595 (Chem. Abstr., 1913, 7, 3348) Search PubMed; T. Weiland, G. Griss and B. Haccius, Arch. Microbiol., 1958, 28, 383 CrossRef; B. Haccius and O. Helfrich, Arch. Microbiol., 1958, 28, 394 CrossRef CAS.
  3. D. T. Gibson and V. Subramanian, in Microbial Degradation of Organic Compounds, ed. D. T. Gibson, Microbiology Series, Marcel Dekker, New York, 1984, vol. 13, ch. 7–13 inclusive Search PubMed.
  4. T. Hudlicky and J. W. Reed, Advances in Asymmetric Synthesis, JAI Press, 1995, vol. 1, p. 271 Search PubMed.
  5. D. T. Gibson, J. R. Koch and R. E. Kallio, Biochemistry, 1968, 7, 2653 CrossRef CAS.
  6. D. T. Gibson, M. Hensley, H. Yoshioka and T. J. Mabry, Biochemistry, 1970, 9, 1626 CrossRef CAS.
  7. D. T. Gibson, G. E. Cardini, F. C. Maseles and R. E. Kallio, Biochemistry, 1970, 9, 1631 CrossRef CAS.
  8. D. T. Gibson, J. R. Koch, C. L. Schuld and R. E. Kallio, Biochemistry, 1968, 7, 3795 CrossRef CAS.
  9. D. T. Gibson, B. Gschwendt, W. K. Yeh and V. M. Kobal, Biochemistry, 1973, 12, 1520 CrossRef CAS.
  10. J. J. DeFrank and D. W. Ribbons, J. Bacteriol., 1977, 129, 1356 CAS; G. J. Wigmore and D. W. Ribbons, J. Bacteriol., 1980, 143, 816 CAS.
  11. S. V. Ley and F. Sternfeld, Tetrahedron, 1989, 45, 3463 CrossRef CAS.
  12. S. V. Ley and A. J. Redgrave, Synlett, 1990, 393 CrossRef CAS.
  13. D. M. Jerina, H. Ziffer and J. W. Daly, J. Am. Chem. Soc., 1970, 92, 1056 CrossRef CAS.
  14. T. Sato, T. Fukuyama, T. Suzuki and H. Yoshikawa, J. Biochem. (Tokyo), 1963, 53, 23 Search PubMed.
  15. M. V. Ganey, R. E. Padykula and G. A. Berchtold, J. Org. Chem., 1989, 54, 2787 CrossRef CAS.
  16. T. Posternak, D. Reymond and H. Friedli, Helv. Chim. Acta, 1955, 38, 205 CrossRef CAS.
  17. N. A. B. Wilson and J. Read, J. Chem. Soc., 1935, 1269 RSC.
  18. H. Suemune, A. Hasegawa and K. Sakai, Tetrahedron: Asymmetry, 1995, 6, 55 CrossRef CAS.
  19. K. L. Platt and F. Oesch, Synthesis, 1977, 449 CrossRef CAS.
  20. B. Beier, K. Schurrle, O. Werbitzky and W. Piepersberg, J. Chem. Soc., Perkin Trans. 1, 1990, 2255 RSC.
  21. H. Secen, Y. Sutbeyaz and M. Balci, Tetrahedron Lett., 1990, 31, 1323 CrossRef CAS.
  22. G. Kresze and W. Dittel, Liebigs Ann. Chem., 1981, 610 Search PubMed.
  23. C. H. Kuo and N. L. Wendler, Tetrahedron Lett., 1984, 25, 2291 CrossRef CAS.
  24. K. Schurrle, B. Beier, O. Werbitzky and W. Piepersberg, Carbohydr. Res., 1991, 212, 321 CrossRef.
  25. H. A. J. Carless and K. Busia, Tetrahedron Lett., 1990, 31, 1617 CrossRef CAS.
  26. H. A. J. Carless and K. Busia, Tetrahedron Lett., 1990, 31, 3449 CrossRef CAS.
  27. H. A. J. Carless and K. Busia, Carbohydr. Res., 1992, 234, 207 CrossRef CAS.
  28. H. B. Mereyala and M. Pannala, Tetrahedron Lett., 1995, 36, 2121 CrossRef CAS.
  29. D. J. R. Massy and P. Wyss, Helv. Chim. Acta, 1990, 73, 1037 CrossRef CAS.
  30. J. P. Vacca, S. J. deSolms, J. R. Hoff, D. C. Billington, R. Baker, J. J. Kulagowski and I. M. Mawer, Tetrahedron, 1989, 45, 5679 CrossRef CAS.
  31. P. J. Garegg and B. Samuelsson, Synthesis, 1979, 469 CrossRef CAS.
  32. D. H. R. Barton, P. Dalko and S. D. Gero, Tetrahedron Lett., 1991, 32, 2471 CrossRef CAS; H. A. Staab and G. Walther, Justus Liebigs Ann. Chem., 1962, 657, 104 CAS.
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