Carbohydrates to carbocycles: an expedient synthesis of pseudo-sugars

(Note: The full text of this document is currently only available in the PDF Version )

A. V. R. L. Sudha and M. Nagarajan


Abstract

A short and versatile synthesis of pseudo-sugars from sugars utilizing the Claisen rearrangement as the key step is described.


References

  1. R. J. Ferrier and S. Middleton, Chem. Rev., 1993, 93, 2779 CrossRef.
  2. R. J. Ferrier, J. Chem. Soc., Perkin Trans. 1, 1979, 1455 RSC.
  3. T. V. RajanBabu, Acc. Chem. Res., 1991, 24, 139 CrossRef CAS.
  4. T. Taguchi, H. Ito, Y. Motoki and Y. Hanzawa, J. Am. Chem. Soc., 1993, 115, 8835 CrossRef CAS.
  5. S. Ogawa, Y. Uematsu, S. Yoshida, N. Sesaki and T. Suami, J. Carbohydr. Chem., 1987, 6, 471 CAS.
  6. T. K. M. Shing and L. H. Wan, Angew. Chem., Int. Ed. Engl., 1995, 34, 1643 CrossRef CAS.
  7. S. Ogawa, Yuki. Gosei Kagaku Kyokai Shi, 1985, 43, 26 Search PubMed.
  8. T. Suami and S. Ogawa, Adv. Carbohydr. Chem. Biochem., 1990, 28, 41 Search PubMed.
  9. D. A. Entwistle and M. Hudlicky, Tetrahedron Lett., 1995, 36, 2591 CrossRef CAS.
  10. L. Pingli and M. Vandewalle, Synlett, 1994, 228 CrossRef CAS.
  11. T. K. M. Shing and Y. Tang, Tetrahedron, 1991, 47, 4571 CrossRef CAS.
  12. T. K. M. Shing, Y. Cui and Y. Tang, J. Chem. Soc., Chem. Commun., 1991, 756 RSC.
  13. R. J. Ferrier and R. Blattner, J. Chem. Soc., Chem. Commun., 1987, 1008 RSC.
  14. G. Büchi and J. E. Powell Jr., J. Am. Chem. Soc., 1967, 89, 4559 CrossRef.
  15. B. Fraser-Reid, R. A. Alonso, G. D. Vite and R. E. McDevitt, J. Org. Chem., 1992, 57, 573 CrossRef.
  16. K. Yamamoto, M. Minato and J. Tsuji, J. Org. Chem., 1990, 55, 766 CrossRef.
  17. F. Fringuelli, R. Germani, F. Pizzo and G. Savelli, Synth Commun., 1989, 19, 1939 CAS.
  18. H. Paulsen and W. von Deyn, Justus Liebigs. Ann. Chem., 1987, 125 Search PubMed.
  19. R. B. Woodward and F. V. Brutcher Jr., J. Am. Chem. Soc., 1958, 80, 209 CrossRef CAS.
Click here to see how this site uses Cookies. View our privacy policy here.