Stereoselective conversion of 2′,3′-dideoxydidehydro carbocyclic nucleosides into 2′-deoxy carbocyclic nucleosides

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James V. Barkley, Anupma Dhanda, May-Britt Nielsen, Stanley M. Roberts, Lars J. S. Knutsen and David R. Varley


Abstract

Treatment of 2′,3′-dideoxydidehydro carbocyclic nucleosides 5–9 with N-bromoacetamide in AcOH gives bromoesters 10–14 with good stereocontrol: debromination and hydrolysis furnishes 2′-deoxy carbocyclic nucleosides, e.g. 22.


References

  1. V. E. Marquez, Adv. Antiviral Drug Dev., 1996, 2, 89 Search PubMed; H. F. Olivo and J. Yu, Tetrahedron: Asymmetry, 1997, 8, 3785 CrossRef CAS; J. Chem. Soc., Perkin Trans. 1, 1998, 391 and references therein Search PubMed.
  2. S. M. Roberts and K. A. Shoberu, J. Chem. Soc., Perkin Trans. 1, 1991, 2605 RSC; E. A. Saville-Jones, S. D. Lindell, N. S. Jennings, J. C. Head and M. J. Ford, J. Chem. Soc., Perkin Trans. 1, 1991, 2603 RSC; C. G. Palmer, R. McCague, G. Ruecroft, S. Savage, S. J. C. Taylor and C. Ries, Tetrahedron Lett., 1996, 37, 4601 CrossRef CAS ; see also V. K. Aggarwal and N. Monteiro, J. Chem. Soc., Perkin Trans. 1, 1997, 2531 Search PubMed; S. E. Ward, A. B. Holmes and R. McCague, Chem. Commun., 1997, 2085 RSC; B. M. Trost, R. Marsden and S. D. Guile, Tetrahedron Lett., 1997, 38, 1707 RSC.
  3. N. Katagiri, Y. Ito, K. Kitano, A. Toyota and C. Kaneko, Chem. Pharm. Bull., 1994, 42, 2653 CAS ; see also G. Poli, Tetrahedron Lett., 1989, 30, 7385 Search PubMed.
  4. R. Marumoto, Y. Yoshioka, Y. Furukawa and M. Honjo, Chem. Pharm. Bull., 1976, 24, 2624 CAS.
  5. D. R. Deardorff, R. G. Linde, A. M. Martin and M. J. Shulman, J. Org. Chem., 1989, 54, 2759 CrossRef CAS.
  6. A. Toyota, Y. Ono and C. Kaneko, Tetrahedron Lett., 1995, 36, 6123 CrossRef CAS.
  7. The corresponding nucleosides have been prepared; see L. J. S. Knutsen, Nucleosides Nucleotides, 1992, 11, 961 Search PubMed it has been reported that 2′-bromo-2′-deoxynucleosides show enhanced stability to 3′-exonucleases: M. Aoyagi, Y. Ueno, A. Ono and A. Matsuda, Bioorg. Med. Chem. Lett., 1996, 6, 1573 CAS.
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