A new method for the conversion of hexose derivatives into substituted pyrrolidines

Heterocycles

Volumn 51, Issue 12, 1999, Pages 2801-2806

  Holzapfel, Cedric W ^a   Crous, Renier ^a   Greyling, Hendrik F ^a   Verdoorn, Gerhard H ^a  

^a UNIVERSITY OF JOHANNESBURG   (South Africa)

Author keywords

[No Author keywords available]

Indexed keywords

HEXOSE; PYRROLIDINE DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHIRALITY; CYCLIZATION; REACTION ANALYSIS; REDUCTION; SYNTHESIS;

EID: 0033372593     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-99-8685     Document Type: Article

References (23)

1. a) R. J. Molyeux, M. Benson, R. Y. Wong, J. E. Tropea, and A. D. Elbein, J. Nat. Prod., 1988, 51, 1198;
2. b) S. Picasso, Y. Chen, and P. Vogel, Carbohydr. Lett., 1994, 1, 1.
3. V. Gross, T. Andus, T. A. Tran-Thi, R. T. Schwarz, K. Decker, and P. C. Heinrich, J. Biol. Chem., 1983, 258, 12203.
4. B. P. Bashyal, G. W. J. Fleet, M. J. Gough, and P. W. Smith, Tetrahedron, 1987, 43, 3083.
5. a) M. Malmberg and N. Rehnberg, Synlett, 1996, April, 361;
6. b) R. O. Martin, L. Liu, and F. Yang, Tetrahedron Lett., 1996, 37, 1991;
7. c) L. Cipolla, L. Lay, F. Nicotra, C. Pangrazio, and L. Panza, Tetrahedron, 1995, 51, 4679.
8. R. Crous, Ph.D. Dissertation, Rand Afrikaans University, 1998.
9. a) G. Buchanan, K. W. Lumbard, R. J. Sturgeon, D. K. Thompson, and R. H. Wightman, J. Chem. Soc., Perkin Trans. I, 1990, 699;
10. b) T. Ishikawa, Y. Tajima, M. Fukui, and S. Saito, Angew. Chem., Int. Ed. Engl., 1996, 35, 1863.
11. J. M. J. Tronchet, G. Zosimo-Landolfo, M. Balkadjian, A. Ricca, M. Zsély, F. Barbalat-Rey, D. Cabrini, P. Lichtle, and M. Geoffroy, Tetrahedron Lett., 1991, 32, 4129.
12. R. Grigg, J. Markandu, T. Perrior, S. Surendrakumar, and W. J. Warnock, Tetrahedron, 1992, 48, 6929.
13. a) R. K. Ness, H. G. Fletcher Jr and C. S. Hudson, J. Am. Chem. Soc., 1950, 72, 2200;
14. b) C. M. McCloskey and G. H. Coleman, J. Am. Chem. Soc., 1944, 66, 349.
15. C. T. Westi, S. J. Donnelly, D. A. Kooistra, and M. P. Doyle, J. Org Chem., 1973, 38, 2675.
16. M. Fujita, H. Oisha, and T. Hiyama, Chem. Lett., 1986, 837.
17. +, 14%), 563 (9%), 105 (100%).
18. +, 2%), 443 (1%), 105 (100%).
19. C. W. Holzapfel and R. Crous, Heterocycles, 1998, 48, 1337.
20. 3): 7.98 (8H, m), 7.51 (12H, m), 6.07 (1H, m), 5.86 (1H, dd, J=9.8 Hz, 1.7 Hz), 5.52 (1H, m), 4.66 (1H, dd, J=1.8 Hz, 12.0 Hz), 4.62 (1H, dd, J=8.0 Hz, 12.0Hz), 3.75
21. +, 56%.
22. K. G. R. Pachler, E. B. Rathbone, G. R. Wodard, and M. Woudenberg, Carbohydr. Res, 1980, 79, 29.
23. K. J. Ryan, H. Arzoumanian, E. M. Acton, and L. Goodman, J. Am. Chem. Soc., 1964, 86, 2497.