Synthesis of casuarines [pentahydroxylated pyrrolizidines] by sodium hydrogen telluride-induced cyclisations of azidodimesylates

Tetrahedron Letters

Volumn 38, Issue 33, 1997, Pages 5869-5872

  Bell, Andrew A ^a   Pickering, Lea ^a   Watson, Alison A ^a,b   Nash, Robert J ^b   Pan, Yuan T ^c   Elbein, Alan D ^c   Fleet, George W J ^a  

^a UNIVERSITY OF OXFORD   (United Kingdom)

^b ABERYSTWYTH UNIVERSITY   (United Kingdom)

^c UNIVERSITY OF ARKANSAS FOR MEDICAL SCIENCES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

POLYOL; PYRROLIZIDINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY;

LATEOLABRAX JAPONICUS;

EID: 0030878235     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01306-3     Document Type: Article

References (28)

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2. Zeng, Y. C., Pan, Y. T., Asano, N., Nash, R. J., Elbein, A. D, Glycobiology, 1997, 7, 297; Kato, A., Asano, N., Kizu, H., Matsui, K., Watson, A. A., Nash, R. J, J. Nat. Prod., 1997, 60, 312.
3. Asano, N., Kizu, H., Oseki, K., Tomioka, E., Matsui, K., Okamoto, M., Baba, M., J. Med. Chem., 1995, 38, 2439.
4. Davis, B., Bell, A. A., Nash, R. J., Watson, A. A., Griffiths, R. C., Jones, M. G., Smith, C., and Fleet, G. W. J., Tetrahedron Lett., 1996, 37, 8565; Shilvock, J. P., Wheatley, J. R., Davis, B., Nash, R. J., Griffiths, R. C., Jones, M. G., Muller, M., Crook, S., Watkin, D. J., Smith, C., Besra, G. S., Brennan, P. J., and Fleet, G. W. J., Tetrahedron Lett., 1996, 37, 8569 and references therein.
5. Davis, B., Bell, A. A., Nash, R. J., Watson, A. A., Griffiths, R. C., Jones, M. G., Smith, C., and Fleet, G. W. J., Tetrahedron Lett., 1996, 37, 8565; Shilvock, J. P., Wheatley, J. R., Davis, B., Nash, R. J., Griffiths, R. C., Jones, M. G., Muller, M., Crook, S., Watkin, D. J., Smith, C., Besra, G. S., Brennan, P. J., and Fleet, G. W. J., Tetrahedron Lett., 1996, 37, 8569 and references therein.
6. Platt, F.M., Neises, G.R., Dwek, R.A., and Butters, T.D., J. Biol. Chem., 1994, 269, 8362; Qiao, L., Murray B.W., Shimazaki, M., Schultz, J., Wong, C-H., J. Am. Chem. Soc., 1996, 118, 7653; C. A. Collyer, J. D. Goldberg, H. Viehmann, D. M. Blow, N. G. Ramsden, G. W. J. Fleet, F. J. Montgomery and P. Grice, Biochemistry, 1992, 31, 12211.
7. Platt, F.M., Neises, G.R., Dwek, R.A., and Butters, T.D., J. Biol. Chem., 1994, 269, 8362; Qiao, L., Murray B.W., Shimazaki, M., Schultz, J., Wong, C-H., J. Am. Chem. Soc., 1996, 118, 7653; C. A. Collyer, J. D. Goldberg, H. Viehmann, D. M. Blow, N. G. Ramsden, G. W. J. Fleet, F. J. Montgomery and P. Grice, Biochemistry, 1992, 31, 12211.
8. Platt, F.M., Neises, G.R., Dwek, R.A., and Butters, T.D., J. Biol. Chem., 1994, 269, 8362; Qiao, L., Murray B.W., Shimazaki, M., Schultz, J., Wong, C-H., J. Am. Chem. Soc., 1996, 118, 7653; C. A. Collyer, J. D. Goldberg, H. Viehmann, D. M. Blow, N. G. Ramsden, G. W. J. Fleet, F. J. Montgomery and P. Grice, Biochemistry, 1992, 31, 12211.
9. Nash, R. J., Watson, A. A., Asano, N., Alkaloids: Chemical & Biological Perspectives, 1996, 11, 346; Winchester B., Fleet, G. W. J., Glycobiology, 1992, 2, 199.
10. Nash, R. J., Watson, A. A., Asano, N., Alkaloids: Chemical & Biological Perspectives, 1996, 11, 346; Winchester B., Fleet, G. W. J., Glycobiology, 1992, 2, 199.
11. Nash, R. J., Thomas, P. I., Waigh, R. D., Fleet, G. W. J., Wormald, M. R., Lilley, P. M. D., Watkin, D. J., Tetrahedron Lett., 1994, 35, 7849.
12. Wormald, M. R., Nash, R. J., Watson, A. A., Bhadoria, B. K., Langford, R., Sims, M., and Fleet, G. W. J., Carbohydr. Lett., 1996, 2, 169.
13. Pan, Y. T., Molyneux, R., Nash, R., Fleet, G. W. J., and Elbein, A. D., manuscript in preparation; Pan, Y. T., Nori, H., Saul, R., Sanford, B. A., Molyneux, R., and Elbein, A. D., Biochemistry, 1983, 22, 3975.
14. Bridges, C. G., Ahmed, S. P., Kang, M. S., Nash, R. J., Porter, E. A., Tyms, A. S., Glycobiology, 1995, 5, 249; Taylor, D.L., Nash, R., Fellows, L.E., Kang, M.S., and Tyms, A.S., Antiviral Chemistry & Chemotherapy, 1992, 3, 273.
15. Bridges, C. G., Ahmed, S. P., Kang, M. S., Nash, R. J., Porter, E. A., Tyms, A. S., Glycobiology, 1995, 5, 249; Taylor, D.L., Nash, R., Fellows, L.E., Kang, M.S., and Tyms, A.S., Antiviral Chemistry & Chemotherapy, 1992, 3, 273.
16. Bell, A. A., Nash, R. J., Fleet, G. W. J., Tetrahedron: Asymmetry, 1996, 7, 595.
17. Bell, A. A., Pickering, L., Watson, A. A., Nash, R. J., Griffiths, R. C., Jones, M. G., Fleet, G. W. J., Tetrahedron Lett., 1996, 37, 8561 and unpublished work.
18. Suzuki, H., Takaoka, K., Chemistry Lett., 1994, 1733.
19. All new compounds in this paper, except where otherwise stated, were oils; all specific rotations [other than where stated] were determined at the concentration in chloroform indicated.
20. 2O): 49.5, 56.9 (2 x t, C-5, C-8), 65.0, 70.0, 72.2, 74.0, 74.5, 78.0 (6 x d, C-1, C-2, C-3, C-6, C-7, C-7a).
21. For related work, see Kruizinga, W. H., Strijlveen, B., and Kellogg, R. M., J. Org. Chem., 1981, 46, 4321; Huffman, J. W., and Desai, R. C., Syn. Commun., 1983, 13, 553; Torisawa, Y., Okabe, H., and Ikegami, S., Chem. Lett., 1984, 1555; Lampe, D., and Potter, B. V. L., Tetrahedron Lett., 1993, 34, 2365.
22. For related work, see Kruizinga, W. H., Strijlveen, B., and Kellogg, R. M., J. Org. Chem., 1981, 46, 4321; Huffman, J. W., and Desai, R. C., Syn. Commun., 1983, 13, 553; Torisawa, Y., Okabe, H., and Ikegami, S., Chem. Lett., 1984, 1555; Lampe, D., and Potter, B. V. L., Tetrahedron Lett., 1993, 34, 2365.
23. For related work, see Kruizinga, W. H., Strijlveen, B., and Kellogg, R. M., J. Org. Chem., 1981, 46, 4321; Huffman, J. W., and Desai, R. C., Syn. Commun., 1983, 13, 553; Torisawa, Y., Okabe, H., and Ikegami, S., Chem. Lett., 1984, 1555; Lampe, D., and Potter, B. V. L., Tetrahedron Lett., 1993, 34, 2365.
24. For related work, see Kruizinga, W. H., Strijlveen, B., and Kellogg, R. M., J. Org. Chem., 1981, 46, 4321; Huffman, J. W., and Desai, R. C., Syn. Commun., 1983, 13, 553; Torisawa, Y., Okabe, H., and Ikegami, S., Chem. Lett., 1984, 1555; Lampe, D., and Potter, B. V. L., Tetrahedron Lett., 1993, 34, 2365.
25. 2O): 56.8 (t, C-5), 63.2 (t, C-8), 69.1 (d, C-7a), 70.6 (d, C-7), 71.7 (d, C-3), 73.9 (d, C-1), 75.5 (d, C-6), 78.6 (d, C-2).
26. 2O): 59.0, 63.3 (2 x t, C-5, C-8), 69.6, 71.5, 73.6, 74.6, 78.2, 79.5 (6 x d, C-1, C-2, C-3, C-6, C-7, C-7a).
27. 2O): 59.0, 63.3 (2 x t, C-5, C-8), 69.6, 71.5, 73.6, 74.6, 78.2, 79.5 (6 x d, C-1, C-2, C-3, C-6, C-7, C-7a).
28. This work has been supported by graduate studentships from the Medical Research Council AIDS Committee, by an NIH grant NIH HL-17783, and by an EPSRC Post-doctoral Fellowship.