The first enantioselective synthesis of 4-acetyl-3(R)- and 3(S)-(hydroxymethyl)-3,4-dihydro-2H-pyrido[3,2-b]oxazine

Tetrahedron Letters

Volumn 45, Issue 7, 2004, Pages 1465-1468

  Henry, N ^a   Guillaumet, G ^b   Pujol, M D ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

^b UNIVERSITÉ D'ORLÉANS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

3 (HYDROXYMETHYL) 3,4 DIHYDRO 2H PYRIDO[3,2 B]OXAZINE; 4 ACETYL 3 (HYDROXYMETHYL) 3,4 DIHYDRO 2H PYRIDO[3,2 B]OXAZINE; OXAZINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BIOAVAILABILITY; CARBON NUCLEAR MAGNETIC RESONANCE; CHIRALITY; ENANTIOSELECTIVITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 1642578964     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.12.030     Document Type: Article

References (24)

1. Valoti E., Pallavicini M., Villa L., Pezzetta D. J. Org. Chem. 66:2001;1018-1025.
2. Giardina D., Bertini R., Brancia E., Brasili L., Melchiorre C. J. Med. Chem. 28:1985;1354-1357.
3. Bozzo C., Pujol M.D. Tetrahedron. 55:1999;11843-11852.
4. Bozzo C., Pujol M.D. Synlett. 2000;550-552.
5. Capilla A.S., Sánchez I., Caignard D.H., Renard P., Pujol M.D. Eur. J. Med. Chem. 36:2001;389-393.
6. Kajino M., Shibouta Y., Nishikawa K., Meguro K. Chem. Pham. Bull. 39:1991;2896-2905.
7. Bourlot A.S., Sánchez I., Dureng G., Guillaumet G., Massingham R., Monteil A., Winslow E., Pujol M.D., Mérour J.Y. J. Med. Chem. 41:1998;3142-3158.
8. Sánchez I., Pujol M.D. Tetrahedron. 55:1999;5593-5598.
9. Comoy C., Benarab A., Monteil A., Leinot M., Massingham R., Guillaumet G. Med. Chem. Res. 6:1996;392-399.
10. Sánchez I., Pujol M.D., Guillaumet G., Massingham R., Monteil A., Dureng G., Winslow E. Sci. Pharm. 68:2000;159-164.
11. Matesanz E., Alcázar J., Andrés J.I., Bartolomé J.M., De Bruyn M., Fernández J., Van Emelen K. Tetrahedron Lett. 44:2003;2275-2277.
12. Arrault A., Touzeau F., Guillaumet G., Léger J.M., Jarry C., Mérour J.Y. Tetrahedron. 58:2003;8145-8152.
13. McClure D.E., Arison B.H., Baldwin J.J. J. Am. Chem. Soc. 101:1979;3666-3668.
14. Klumder J.M., Ko S.Y., Sharpless K.B. J. Org. Chem. 51:1986;3710-3712.
15. Delgado A., Leclerc G., Lobato M.C., Mauleón D. Tetrahedron Lett. 29:1988;3671-3674.
16. Ellis M.-K., Golding B.T. Org. Synth. 63:1984;140-143.
17. Golding B.T., Hall D.R., Sakrikar S. J. Chem. Soc., Perkin Trans. 1. 1973;1214-1220.
18. Nelson W.L., Wennerstrom J.E. J. Med. Chem. 20:1977;880-885.
19. Raban M., Mislow K. Topics in Stereochem. 2:1967;199-202.
20. Chem. Abs. 68:1968;43235.
21. Lamshoft M., Schmickler H., Marner F.J. Eur. J. Org. Chem. 2003;727-733.
22. Trost B.M., Belletire J.L., Godleski S., McDougal P.G., Balkovec J.M., Baldwin J.J., Christy M.E., Ponticello G.S., Varga S.L., Springer J.P. J. Org. Chem. 51:1986;2370-2374.
23. Abad J.L., Casas J., Sánchez-Baeza F., Messeguer A. J. Org. Chem. 60:1995;3648-3656.
24. 2: C, 55. 26; H, 5.30; N, 18.41. Found: C, 55.58; H, 5.74%; N, 18.12.