C5-homologization of ubiquinone-9 and ubiquinone-10 using sulfur-containing synthons

  • A. B. Veselovskii
  • A. M. Moiseenkov
  • T. M. Filippova
  • E. A. Obol'nikova
  • G. I. Samokhvalov
Organic Chemistry
  • 22 Downloads

Conclusions

A seven-stage method has been developed for the transformation of ubiquinone-9 to ubiquinone-10 using sulfur-containing synthons as the key step; the most effective synthon was found to be prenyl phenyl sulfide. The analogous homologization of solanesol and decaprenol using an isoprenyl trans-C5-hydroxysulfone was also examined.

Keywords

Sulfide Phenyl Prenyl Phenyl Sulfide Isoprenyl 

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Literature cited

  1. 1.
    A. M. Moiseenkov, A. B. Veselovskii, and T. M. Filippova, Izv. Akad. Nauk SSSR, Ser. Khim., 2086 (1987).Google Scholar
  2. 2.
    A. I. Kozhukhova, E. A. Obol'nikova, and T. M. Filippova, Zh. Org. Khim.,20, 1683 (1984).Google Scholar
  3. 3.
    S. Terao, M. Shiraishi, K. Kato, et al., J. Chem. Soc., Perkin Trans.,1, 2909 (1982).Google Scholar
  4. 4.
    K. Sato, O. Miyamoto, S. Inoue, et al., J. Chem. Soc., Chem. Commun., 153 (1982).Google Scholar
  5. 5.
    M. Julia, D. Uguen, and A. Callipolitis, Bull. Soc. Chim. France, 519 (1976).Google Scholar
  6. 6.
    K. Shimada, M. Kodama, and S. Ito, Tetrahedron Lett.,22, 4275 (1981).Google Scholar
  7. 7.
    L. J. Altman, L. Ash, S. Marson, Synthesis, 129 (1974).Google Scholar
  8. 8.
    Y. Masaki, K. Hashimoto, and K. Kaji, Chem. Pharm. Bull.,32, 3959 (1984).Google Scholar
  9. 9.
    I. Yoshizawa, H. Toyofuku, K. Tashibana, and T. Kuroda, Chem. Lett., 1131 (1982).Google Scholar
  10. 10.
    K. Sato, S. Inoue, A. Onishi, N. Uchida, and N. Minowa, J. Chem. Soc., Perkin Trans.,1, 761 (1981).Google Scholar
  11. 11.
    D. K. Dalling and D. M. Grant, J. Am. Chem. Soc.,94, 5318 (1972).Google Scholar
  12. 12.
    A. M. Moiseenkov and E. V. Polunin, Izv. Akad. Nauk SSSR, Ser. Khim., 1562 (1983).Google Scholar
  13. 13.
    C. V. N. Rao and M. K. Chakrpborty, Res. Ind., 24, 83 (1979).Google Scholar
  14. 14.
    J. Martell and C. Huynh, Bull. Soc Chim. France, 985 (1967).Google Scholar
  15. 15.
    W. E. Parham and S. H. Groen, J. Org. Chem.,31, 1694 (1966).Google Scholar

Copyright information

© Plenum Publishing Corporation 1988

Authors and Affiliations

  • A. B. Veselovskii
    • 1
    • 2
  • A. M. Moiseenkov
    • 1
    • 2
  • T. M. Filippova
    • 1
    • 2
  • E. A. Obol'nikova
    • 1
    • 2
  • G. I. Samokhvalov
    • 1
    • 2
  1. 1.N. D. Zelinskii Institute of Organic ChemistryAcademy of Sciences of the USSRMoscow
  2. 2.“Vitamins” Scientific Industrial AssociationMoscow

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