Synthesis of carbasugars from aldonolactones. Part II. Preparation of polyhydroxy/aminocyclopentanes functionalised at all five ring carbons

Abstract

Starting from (1R,5R,8R)-8-acetoxy-2-oxabicyclo[3.3.0]oct-6-en-3-one 4 the syntheses of 5-deoxy-4a(R)-hydroxy-4a-carba-α-D-ribo-hexofuranose 17, 5-deoxy-4a(R)-hydroxy-4a-carba-α-D-lyxo-hexofuranose 21, 5-deoxy-4a(R)-hydroxy-4a-carba-α-D-xylo-hexofuranose 23 and 4a(R)-hydroxy-2-amino-2,5-dideoxy-4a(R)-hydroxy-4a-carba-α-D-arabino-hexofuranose 1 have been achieved. The methodology included OsO₄-catalysed dihydroxylation as well as regioselective epoxide opening followed by calcium borohydride reduction of the lactone moiety.

References

1. Part I, S. K. Johansen, H. T. Kornø and I. Lundt, Synthesis, 1999, 171.
2. S. K. Johansen and I. Lundt, presented in part at the XIXth International Carbohydrate Symposium (ICS XIX), San Diego, CA, 1998(abstract BP 221).
3. For the use of the carba prefix, see: C. Marschner, J. Baumgartner and H. Griengl, J. Org. Chem., 1995, 60, 5224; and IUPAC rule: 2-carb-34.2 (Pure Appl. Chem., 1996, 68, 1919).
4. M. T. Crimmins, Tetrahedron, 1998, 54, 9229.
5. For a recent synthesis, see: Y. Tokoro and Y. Kobayashi, Chem. Commun., 1999, 807.
6. For a recent synthesis, see: H. F. Olivo and J. Yu, J. Chem. Soc., Perkin Trans. 1, 1998, 391.
7. A. Toyota, N. Katagiri and C. Kaneko, Heterocycles, 1994, 38, 27.
8. A. Berecibar, C. Grandjean and A. Siriwardena, Chem. Rev., 1999, 99, 779; Carbohydrate Mimics, ed. Y. Chapleur, Wiley, Weinheim, 1998.
9. For a recent synthesis see: R. Ling, P. S. Mariano and B. Ganem, J. Org. Chem., 1998, 63, 6072.
10. For a recent synthesis see: D. J. Kassab and B. Ganem, J. Org. Chem., 1999, 64, 1782.
11. For a recent synthesis see: A. Boiron, P. Zillig, D. Faber and B. Giese, J. Org. Chem., 1998, 63, 5877.
12. R. A. Farr, N. P. Peet and M. S. Kang, Tetrahedron Lett., 1990, 31, 7109.
13. A. Blaser and J.-L. Reymond, Helv. Chim. Acta, 1999, 82, 760.
14. A. M. Horneman, I. Lundt and I. Søtofte, Synlett, 1995, 918; A. M. Horneman and I. Lundt, Tetrahedron, 1997, 53, 6879 (J. Org. Chem., 1998, 63, 1919).
15. I. Lundt, Top. Curr. Chem., 1997, 187, 117.
16. K. B. Sharpless and T. R. Verhoeven, Aldrichim. Acta, 1979, 12, 63.
17. S. Daluge and R. Vince, J. Org. Chem., 1978, 43, 2311.
18. S. Ogawa and K. Washida, Eur. J. Org. Chem., 1998, 1929.
19. Anhydrous TBHP was prepared following the procedure by J. G. Hill, B. E. Rossiter and K. B. Sharpless, J. Org. Chem., 1983, 48, 3607.