An efficient semisynthesis of 7-deoxypaclitaxel from taxine

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Radomir Matović and Radomir N. Saičić


Abstract

Highly cytotoxic 7-deoxypaclitaxel analogues are obtained by a semisynthesis starting from taxine—the most abundant naturally occurring taxane diterpene fraction.


References

  1. Taxol®: Science and Applications, ed. M. Suffness, CRC Press, Boca Raton, 1995, and references cited therein Search PubMedIsolation and structure elucidation: M. C. Wani, H. L. Taylor, M. E. Wall, P. Coggon and A. T. McPhail, J. Am. Chem. Soc., 1971, 93, 2325 Search PubMed Total syntheses: K. C. Nicolaou, H. Ueno, J.-J. Liu, P. G. Nantermet, Z. Yang, J. Renaud, K. Paulvannan and R. Chadha, J. Am. Chem. Soc., 1995, 117, 653 Search PubMed; R. A. Holton, H.-B. Kim, C. Somoza, F. Liang, R. J. Biediger, P. D. Boatman, M. Shindo, C. C. Smith, S. Kim, H. Nadizadeh, Y. Suzuki, C. Tao, P. Vu, S. Tang, P. Zhang, K. K. Murthi, L. N. Gentile and J. H. Liu, J. Am. Chem. Soc., 1994, 116, 1599 CrossRef; S. J. Danishefsky, J. J. Masters, W. B. Young, J. T. Link, L. B. Snyder, T. V. Magee, D. K. Jung, R. C. A. Isaacs, W. G. Bornmann, C. A. Alaimo, C. A. Coburn and M. J. Di Grandi, J. Am. Chem. Soc., 1996, 118, 2843 Search PubMed; P. A. Wender, N. F. Badham, S. P. Conway, P. E. Floreancig, T. E. Glass, J. B. Houze, N. E. Krauss, D. Lae, D. G. Marquess, P. L. McGrane, W. Meng, M. G. Natchus, A. J. Shuker, J. C. Sutton and R. E. Taylor, J. Am. Chem. Soc., 1997, 119, 2757 CrossRef CAS.
  2. J.-N. Denis, A. E. Greene, D. Guenard, F. Gueritte-Voegelein, L. Mangatal and P. Potier, J. Am. Chem. Soc., 1998, 110, 5917.
  3. G. Chauviere, D. Guenard, F. Picot, V. Senilh and P. Potier, C. R. Seances Acad. Sci., Ser. 2, 1981, 293, 501 Search PubMed; K. M. Witherup, S. A. Look, M. W. Stasko, T. J. Ghiorzi, G. M. Mushik and G. M. Cragg, J. Nat. Prod., 1990, 53, 1249 CAS see also ref. 2.
  4. H. Lucas, Arch. Pharm., 1856, 14, 438 Search PubMed; G. Appendino, in Alkaloids: Chemical and Biological Perspectives, ed., S. W. Pelletier, Pergamon, Oxford, 1996, vol. 11, p. 237 Search PubMed; L. H. D. Jenniskens, E. L. M. van Rosendaal, T. A. van Beek, P. H. G. Wiegerinck and H. W. Scheeren, J. Nat. Prod., 1996, 59, 117 Search PubMed for an alternative isolation procedure, see ref. 7(a).
  5. L. Ettouati, A. Ahond, C. Poupat and P. Potier, J. Nat. Prod., 1991, 54, 1455 CrossRef CAS; in some specimens of Taxus baccata a content of taxine as high as 17 g kg–1 was found, 10 g being taxine B; the authors are grateful to Dr A. Ahond and Dr C. Poupat for this personal communication.
  6. A. G. Chaudhary, J. M. Rimoldi and D. G. I. Kingston, J. Org. Chem., 1993, 58, 3798 CrossRef CAS; S.-H. Chen, S. Huang, J. Kant, C. Fairchild, J. Wei and V. Farina, J. Org. Chem., 1993, 58, 5028 CrossRef CAS; V. Farina, S.-H. Chen, D. R. Langley, M. D. Wittman, J. Kant and D. Vyas, Eur. Pat. Appl., EP 590,267/6 apr, 1994(Chem. Abstr., 1994, 121, 205747n) Search PubMed.
  7. (a) L. Ettouati, A. Ahond, C. Poupat and P. Potier, Tetrahedron, 1991, 47, 9823 CrossRef CAS; (b) P. H. G. Wiegerinck, L. Fluks, J. B. Hammink, S. J. E. Mulders, F. M. H. de Groot, H. L. M. van Rosendaal and H. W. Sheeren, J. Org. Chem., 1996, 61, 7092 CrossRef CAS; (c) I. Fenoglio, G. M. Nano, D. G. V. Velde and G. Appendino, Tetrahedron Lett., 1996, 37, 3203 CrossRef CAS; (d) H. Poujol, A. A. Mourabit, A. Ahond, C. Poupat and P. Potier, Tetrahedron, 1997, 53, 12 575 CrossRef CAS and references cited therein.
  8. While this work was in progress, the first semisynthesis of 7-deoxybaccatin from 3 was reported, in 15 steps and 1.7% overall yield, see ref. 7(d).
  9. J.-N. Denis, A. Correa and A. E. Greene, J. Org. Chem., 1990, 55, 1957 CrossRef CAS.
  10. Spectral data identical to those reported in ref. 7(d).
  11. A. M. Kanazawa, J.-N. Denis and A. E. Greene, Chem. Commun., 1994, 2591 RSC.
  12. 1H NMR data identical to those reported in ref. 6.