Chirospecific synthesis of 1,4-dideoxy-1,4-imino-D-arabinitol and 1,4-dideoxy-1,4-imino-L-xylitol via one-pot cyclisation

Abstract

The multi-protected compounds 4 and 5 were treated with 20% iodine in methanol to give 1,4-dideoxy-1,4-imino-D-arabinitol 1 and 1,4-dideoxy-1,4-imino-L-xylitol 2 directly. Iodine was an efficient catalyst for deprotection of O-isopropylidene, O-(tert-butyldimethylsilyl), N-(9-phenylfluoren-9-yl) and N-benzyloxycarbonyl groups, resulting in intramolecular cyclisation.

References

1. (a) G. W. J. Fleet, S. J. Nicolas, P. W. Smith, S. V. Evans, L. E. Fellows and R. J. Nash, Tetrahedron Lett., 1985, 26, 3127; (b) N. Asano, K. Oseki, H. Kizu and K. Matsui, J. Med. Chem., 1994, 37, 3701; (c) N. Asano, H. Kizu, K. Oseki, E. Tomioka, K. Matsui, M. Okamoto and M. Baba, J. Med. Chem., 1995, 38, 2349.
2. (a) R. J. Nash, E. A. Bell and J. M. Williams, Phytochemistry, 1985, 24, 1620; (b) J. Furukawa, S. Okuda, K. Saito and S. I. Hatanaka, Phytochemistry, 1985, 24, 593.
3. For a preparation of D-iminoarabinitol (a) G. W. J. Fleet and P. W. Smith, Tetrahedron, 1986, 42, 5685; (b) T. Ziegler, A. Straub and F. Effenberger, Angew. Chem., Int. Ed. Engl., 1988, 27, 716; (c) G. W. J. Fleet and D. R. Witty, Tetrahedron: Asymmetry, 1990, 1, 119; (d) T. Kajimoto, L. Chen, K. K.-C. Liu and C.-H. Wong, J. Am. Chem. Soc., 1991, 113, 6687For a preparation of D-iminoxylitol (e) J. G. Buchanan, K. W. Lumbard, R. J. Sturgeon, D. K. Thompson and R. H. Wightman, J. Chem. Soc., Perkin Trans. 1, 1990, 699; (f) Q. Meng and M. Hesse, Helv. Chim. Acta, 1991, 74, 445; (g) Y. Huang and D. R. Dalton, J. Org. Chem., 1997, 62, 372.
4. W. D. Lubell and H. Rapoport, J. Am. Chem. Soc., 1987, 109, 236.
5. (a) R. Csuk, M. Hugener and A. Vasella, Helv. Chim. Acta, 1988, 71, 609; (b) M. Gerspacher and H. Rapoport, J. Org. Chem., 1991, 56, 3700.
6. K. H. Park, Y. J. Yoon and S. G. Lee, Tetrahedron Lett., 1994, 35, 9737.
7. (a) F. R. Cruickshank and S. W. Benson, J. Phys. Chem., 1969, 73, 733; (b) A. R. Vaino and W. A. Szarek, Chem. Commun., 1996, 2351.
8. I. Pastuszak, R. J. Molyneux, L. F. James and A. D. Elbein, Biochemistry, 1990, 29, 1886.