Nitrile oxide cycloadditions to olefinated sugars

Tetrahedron Letters

Volumn 44, Issue 5, 2003, Pages 1071-1074

  Colinas, Pedro A ^a   Jäger, Volker ^b   Lieberknecht, Albrecht ^a,b   Bravo, Rodolfo D ^a  

^a FACULTAD DE CIENCIAS EXACTAS   (Argentina)

^b UNIVERSITY OF STUTTGART   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOHYDRATE DERIVATIVE; ISOXAZOLINE DERIVATIVE;

ARTICLE; CHROMATOGRAPHY; CYCLOADDITION; DRUG SYNTHESIS; ISOLATION PROCEDURE; METABOLITE; MICROWAVE IRRADIATION; NONHUMAN; STEREOCHEMISTRY; WITTIG REACTION;

EID: 0037467864     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)02665-5     Document Type: Article

References (20)

1. Perron F., Abizati K.F. Chem. Rev. 89:1989;1617-1661.
2. Ichiba T., Scheuer P.J. J. Org. Chem. 58:1993;4149-4150.
3. Liu S., Fu X., Schmitz F.J., Kelly-Borges M. J. Nat. Prod. 60:1997;614-615.
4. Lacy C., Scheuer P.J. J. Nat. Prod. 63:2000;119-121.
5. Lieberknecht A., Griesser H., Bravo R.D., Colinas P.A., Grigera R.J. Tetrahedron. 54:1998;3159-3168;
6. For other syntheses see: Somsák, L. Chem. Rev. 2001, 101, 81-135 and references therein; Griffin, F. K.; Paterson, D. E.; Murphy, P. V.; Taylor, R. K. Eur. J. Org. Chem. 2002, 1305-1322. Cf. Cycloadditions to furan: Müller, I. Dissertation, Würzburg, 1984; Jäger, V.; Müller, I. Tetrahedron 1985, 41, 3519-3528.
7. For other syntheses see: Somsák, L. Chem. Rev. 2001, 101, 81-135 and references therein; Griffin, F. K.; Paterson, D. E.; Murphy, P. V.; Taylor, R. K. Eur. J. Org. Chem. 2002, 1305-1322. Cf. Cycloadditions to furan: Müller, I. Dissertation, Würzburg, 1984; Jäger, V.; Müller, I. Tetrahedron 1985, 41, 3519-3528.
8. For other syntheses see: Somsák, L. Chem. Rev. 2001, 101, 81-135 and references therein; Griffin, F. K.; Paterson, D. E.; Murphy, P. V.; Taylor, R. K. Eur. J. Org. Chem. 2002, 1305-1322. Cf. Cycloadditions to furan: Müller, I. Dissertation, Würzburg, 1984; Jäger, V.; Müller, I. Tetrahedron 1985, 41, 3519-3528.
9. For other syntheses see: Somsák, L. Chem. Rev. 2001, 101, 81-135 and references therein; Griffin, F. K.; Paterson, D. E.; Murphy, P. V.; Taylor, R. K. Eur. J. Org. Chem. 2002, 1305-1322. Cf. Cycloadditions to furan: Müller, I. Dissertation, Würzburg, 1984; Jäger, V.; Müller, I. Tetrahedron 1985, 41, 3519-3528.
10. Lieberknecht A., Griesser H., Krämer B., Bravo R.D., Colinas P.A., Grigera R.J. Tetrahedron. 55:1999;6475-6482.
11. RajanBabu T.V., Reddy G.S. J. Org. Chem. 51:1986;5458-5461.
12. The E and Z configurations were assigned on the basis of the chemical shifts of the vinyl protons, according to increment calculations done for related olefins: Pascual, C.; Meier, J.; Simon, W. Helv. Chim. Acta 1969, 49, 164-168; Pretsch, E.; Clerc, T.; Seibl, J.; Simon, W. Strukturauflklärung organischer Verbindungen, 3rd ed.; Springer: Berlin-Heidelberg-New York, 1986. Also the assignment was confirmed by comparison with earlier exo-glycals prepared by us: Refs. 3a and 4.
13. The E and Z configurations were assigned on the basis of the chemical shifts of the vinyl protons, according to increment calculations done for related olefins: Pascual, C.; Meier, J.; Simon, W. Helv. Chim. Acta 1969, 49, 164-168; Pretsch, E.; Clerc, T.; Seibl, J.; Simon, W. Strukturauflklärung organischer Verbindungen, 3rd ed.; Springer: Berlin-Heidelberg-New York, 1986. Also the assignment was confirmed by comparison with earlier exo-glycals prepared by us: Refs. 3a and 4.
14. 5: C, 77.33; H, 7.15; N, 2.31. Found: C, 77.20; H, 7.04; N, 2.25.
15. 7: C, 72.12; H, 4.95; N, 2.55. Found: C, 71.98; H, 4.86; N, 2.51.
16. Loupy A., Petit A., Hamelin J., Texier-Boullet F., Jacquault P., Mathé D. Synthesis. 9:1998;1213-1234.
17. Touaux B., Klein B., Texier-Boullet F., Hamelin J. J. Chem. Res. (S). 1994;116-117.
18. Touaux B., Texier-Boullet F., Hamelin J. Heteroatom Chem. 9:1998;351-354.
19. 3 previously dried. The mixture was then irradiated for the given time and power. Then the mixture was extracted with methylenchloride, and, after removal of the solvent, the residue was purified by chromatography on silica gel (eluent: hexane/ethyl acetate 9:1).
20. Jäger, V.; Colinas, P. A. Nitrile Oxides. In The Chemistry of Heterocyclic Compounds, Vol. 59: Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products; Padwa, A.; Pearson, W., Eds.; Wiley, 2002.