A facile route to diastereomerically pure analogues of castanospermine and australine

Tetrahedron Letters

Volumn 37, Issue 1, 1996, Pages 49-52

  Marek, D ^a   Wadouachi, A ^a   Uzan, R ^a   Beaupere, D ^a   Nowogrocki, G ^b   Laplace, G ^c  

^a UNIVERSITÉ DE PICARDIE JULES VERNE   (France)

^b Ecole Nationale Superieure de Chimie de Lille   (France)

^c NONE

Author keywords

[No Author keywords available]

Indexed keywords

AUSTRALINE DERIVATIVE; CASTANOSPERMINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030029774     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(95)02093-4     Document Type: Article

References (19)

1. (a) Klein, A.D. ; Molyneux, R. J. Alkaloids : Chemical and Biological Perspectives ; S. W. Pelletier Ed. Wiley, NY, 1987, 5,1-54.
2. (b) Molyneux, R. J.; Benson, M.; Wong, R.Y.; Tropea, J.E.; Elbein, A.D. J. Natural Products 1988, 51, 1198-1206.
3. (c) Picasso, S.; Chen, Y.; Vogel, P. Carbohydr. Lett., 1994, 1, 1-8.
4. Burgess, K.; Henderson, I. Tetrahedron , 1992, 48, 4045-4066.
5. Siriwardena, A. H.; Chiaroni, A.; Riche, C.; Grierson, D. S. J. Org. Chem. 1992, 57, 5661-5666.
6. Wadouachi, A.; Beaupère, D.; Uzan, R.; Stasik, J.; Ewing, D. F.; Mackenzie, G. Carbohydr. Res., 1994, 262, 147-154.
7. Levene, P. A.; Stiller, E. T. J. Biol. Chem., 1933, 187-201.
8. (a) Mitsunobu, O. Synthesis 1981.
9. (b) Bernotas, R. C.; Cube, R. V. Tetrahedron Lett., 1991, 32, 161-164.
10. 4NS : C 52.73, H 6.95, N 5.12, S 11.73. Found : C 52.77, H 6.83, N 5.38, S 11.62.
11. 3) revealed two signals at 47,0 ppm et 49,2 ppm corresponding respectively to C-4 and C-3 of N-carbobenzyloxy-2-(3,4-anhydro-1,2-O-isopropylidene-D-ribotetrahydroxybutyl) thiazolidine.
12. (a) Barbry, D.; Couturier, D.; Ricart, G. Synthesis , 1980, 387-389.
13. (b) Johnson, C. R.; Golebiowski, A.; Sundram, H.; Miller, M. W., Dwaihy, R. L. Tetrahedron Lett., 1995, 36, 653-654.
14. (c) Zhou, W. S.; Xie, W. G.; Lu, Z. H.; Pan, X.F. Tetrahedron Lett., 1995, 36, 1291-1294.
15. 3 reduced to 37% the overall yield and favored the formation of by-product as chlorinated derivative.
16. Martin, O. R.; Saavedra, O. M. Tetrahedron Lett., 1995, 36, 799-802.
17. Hurt, J.A.; Roush, W. R. Tetrahedron Lett., 1995, 36, 501-504.
18. W=0.028 and GoF=1.97. The enantiomorph configuration gave GoF=1.98.
19. 8a,8=6.2 and 6.9 Hz respectively.