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DOI: 10.1039/A700142H (Paper) Reference Section for: J. Chem. Soc., Perkin Trans. 1, 1997, 1449-1456

A new synthetic method for the preparation of amino sugars through an allyl cyanate-to-isocyanate rearrangement

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Yoshiyasu Ichikawa, Masafumi Osada, Ikuko I. Ohtani and Minoru Isobe

Abstract

A new approach for the synthesis of amino sugars using an allyl cyanate-to-isocyanate rearrangement has been developed. The key feature in this method involves introduction of the nitrogen substituent into the pyranose framework by [3,3] sigmatropic rearrangement of an allyl cyanate. Subsequent functionalization of the allylamine moiety by either hydroxylation or cyclofunctionalization completes the synthesis of two amino sugars, D-perosamine and D-vicenisamine.

References

  1. Y. Ichikawa, Synlett, 1991, 238 CrossRef CAS.
  2. Y. Ichikawa, K. Tsuboi and M. Isobe, J. Chem. Soc., Perkin Trans. 1, 1994, 2791 RSC.
  3. (a) Y. Ichikawa, C. Kobayashi and M. Isobe, Synlett, 1994, 919 CrossRef CAS; (b) Y. Ichikawa, C. Kobayashi and M. Isobe, J. Chem. Soc., Perkin Trans. 1, 1996, 377 RSC.
  4. Y. Ichikawa, M. Yamazaki and M. Isobe, J. Chem. Soc., Perkin Trans. 1, 1993, 2429 RSC.
  5. C.-H. Lee and C. P. Schaffner, Tetrahedron Lett., 1966, 5837 CrossRef CAS.
  6. J. W. Redmond, FEBS Lett., 1975, 50, 147 CrossRef CAS.
  7. M. Caroff, D. R. Bundle and M. B. Perry, Eur. J. Biochem., 1984, 139, 195 CAS.
  8. M. Caroff, D. R. Bundle, M. B. Perry, J. W. Cherwonogrodzky and J. R. Dunch, Infect. Immun., 1984, 46, 384 CAS.
  9. J. S. Brimacombe, O. A. Ching and M. Stacey, J. Chem. Soc. C, 1969, 1270 RSC.
  10. (a) C. L. Stevens, R. P. Glinski and K. G. Taylor, J. Org. Chem., 1968, 33, 1586 CrossRef CAS; (b) C. L. Stevens, R. P. Glinski, K. G. Taylor, P. Blumbergs and S. K. Gupta, J. Am. Chem. Soc., 1970, 92, 3160 CrossRef CAS.
  11. M. J. Eis and B. Ganem, Carbohydr. Res., 1988, 176, 316 CrossRef CAS.
  12. (a) M. Isobe, Y. Ichikawa and T. Goto, Tetrahedron Lett., 1985, 26, 5199 CrossRef CAS; (b) Y. Ichikawa, M. Isobe, D.-L. Bai and T. Goto, Tetrahedron, 1987, 43, 4737 CrossRef CAS.
  13. V. VanRheenen, R. C. Kelly and D. Y. Cha, Tetrahedron Lett., 1976, 23, 1973 CrossRef.
  14. K. Shindo, M. Kamishohara, A. Odagawa, M. Matsuoka and H. Kawai, J. Antibiot., 1993, 46, 1076 CAS.
  15. (a) A. J. Bloodworth and A. Davies, J. Chem. Soc. C, 1965, 5238 Search PubMed; (b) A. Davies, Synthesis, 1969, 56 CrossRef CAS.
  16. L. A. Clizbe and L. E. Overman, Org. Synth., 1988, Coll Vol., 507 Search PubMed.
  17. (a) M. George, D. Mackay and B. Fraser-Reid, Can. J. Chem., 1984, 62, 1539; (b) G. Cardillo and M. Orena, Tetrahedron, 1990, 46, 3321 CrossRef CAS.
  18. B. Simonot and G. Rousseau, J. Org. Chem., 1994, 59, 5912 CrossRef CAS.
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