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DOI: 10.1039/A702545I (Paper) Reference Section for: J. Chem. Soc., Perkin Trans. 1, 1997, 2731-2738

Total synthesis of C31-methyl ketone apocarotenoids. Part 4. First total synthesis of (3S,5R,6R)-paracentrone

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Jarle André Haugan

Abstract

Optically active (all-E)-(3S,5R,6R)-paracentrone has been prepared by total synthesis for the first time, in 3% overall yield over 13 linear steps from the readily available (4R,6R)-actinol, (2E)-3-methylpent-2-en-4-yn-1-ol, (all-E)-2,7-dimethylocta-2,4,6-triene-1,8-dial and 1,1-dimethoxypropan-2-one. All spectral data for synthetic (all-E)-(3S,5R,6R)-paracentrone are in accordance with data reported for the natural compound.

References

  1. G. Galasko, J. Hora, T. P. Toube, B. C. L. Weedon, D. André, M. Barbier, E. Lederer and V. R. Villanueva, J. Chem. Soc. C, 1969, 1264 RSC.
  2. O. Straub, in: H. Pfander, M. Gerspacher, M. Rychener and R. Schwabe, eds., Key to Carotenoids, Birkhäuser, Basel, 2nd edn., 1987 Search PubMed.
  3. L. Bartlett, W. Klyne, W. P. Mose, P. M. Scopes, G. Galasko, A. K. Mallams, B. C. L. Weedon, J. Szabolcs and G. Tóth, J. Chem. Soc. C, 1969, 2527 RSC.
  4. T. E. DeVille, M. B. Hursthouse, S. W. Russell and B. C. L. Weedon, Chem. Commun, 1969, 754 RSC.
  5. J. R. Hlubucek, J. Hora, S. W. Russell, T. P. Toube and B. C. L. Weedon, J. Chem. Soc., Perkin Trans. 1, 1974, 848 RSC.
  6. J. Hora, T. P. Toube and B. C. L. Weedon, J. Chem. Soc. C, 1970, 241 RSC.
  7. T. Matsuno, M. Ookubo and T. Komori, J. Nat. Prod., 1985, 48, 606 CrossRef CAS.
  8. J. A. Haugan, Tetrahedron Lett., 1996, 3887 CrossRef CAS.
  9. J. A. Haugan, Acta Chem. Scand., in the press Search PubMed.
  10. J. A. Haugan, E. Lobkovsky and S. Liaaen-Jensen, Acta Chem. Scand., in the press Search PubMed.
  11. A. Baumeler and C. H. Eugster, Helv. Chim. Acta, 1991, 74, 469 CrossRef CAS.
  12. A. Baumeler and C. H. Eugster, Helv. Chim. Acta, 1992, 75, 773 CrossRef CAS.
  13. Y. Yamano and M. Ito, J. Chem. Soc., Perkin Trans. 1, 1993, 1599 RSC.
  14. Y. Yamano, C. Tode and M. Ito, J. Chem. Soc., Perkin Trans. 1, 1995, 1895 RSC.
  15. J. A. Haugan, Acta Chem. Scand., 1994, 48, 657 CAS.
  16. B. O. Brown and B. C. L. Weedon, Finn. Chem. Lett., 1984, 102 Search PubMed.
  17. J. A. Haugan and S. Liaaen-Jensen, Acta Chem. Scand., 1995, 49, 271 CAS.
  18. J. A. Haugan, P. Kongsaeree, J. Clardy and S. Liaaen-Jensen, Tetrahedron: Asymmetry, 1994, 5, 1367 CrossRef CAS.
  19. J. A. Haugan and S. Liaaen-Jensen, Acta Chem. Scand., 1994, 48, 899 CAS.
  20. M. Ito, Y. Hirata, K. Tsukida, N. Tanaka, K. Hamada, R. Hino and T. Fujiwara, Chem. Pharm. Bull., 1988, 36, 3328 CAS.
  21. K. Bernhard, unpublished resultscf. E. Widmer, Pure and Appl. Chem., 1985, 57, 741 Search PubMed.
  22. K. Noack, in: G. Britton and T. W. Goodwin, eds., Carotenoids chemistry and biochemistry, Pergamon, Oxford, 1982, p. 135 Search PubMed.
  23. K. Noack, R. Buchecker, in: G. Britton, S. Liaaen-Jensen and H. Pfander, eds., Carotenoids, Vol. 1B, Spectroscopy, Birkhäuser, Basel, 1995, p. 63 Search PubMed.
  24. J. A. Haugan, G. Englert, E. Glinz and S. Liaaen-Jensen, Acta Chem. Scand., 1992, 46, 389 CAS.
  25. J. A. Haugan, Dr.ing. thesis, University of Trondheim-NTH, 1994.
  26. B. Ke, F. Imsgard, H. Kjøsen and S. Liaaen-Jensen, Biochim. Biophys. Acta, 1970, 210, 139 CAS.
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