BF3·Et2O-induced Beckmann rearrangement of 23-hydroxyiminosapogenins. A shortcut to bisnorcholanic lactones

Tetrahedron Letters

Volumn 47, Issue 30, 2006, Pages 5351-5353

  Iglesias Arteaga, Martín A ^a   Alvarado Nuño, Angel A ^a  

^a UNIVERSIDAD NACIONAL AUTÓNOMA DE MÉXICO   (Mexico)

Author keywords

[No Author keywords available]

Indexed keywords

5ALPHA DIHYDROVESPERTILIN ACETATE; ACETIC ACID; BORON TRIFLUORIDE; LACTONE DERIVATIVE; SAPOGENIN; TOLUENE; UNCLASSIFIED DRUG; VESPERTILIN ACETATE;

ARTICLE; BECKMANN REARRANGEMENT; DRUG SYNTHESIS;

EID: 33745213124     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.05.118     Document Type: Article

References (24)

1. González A.G., García C., Freire R., and Suárez E. An. Quim. 67 (1971) 433-439
2. Ahmad V.U., Khaliq-uz-Zaman S.M., Shameel S., Perveen S., and Ali Z. Phytochemistry 50 (1998) 481-484
3. Zheng Q.A., Zhang Y.J., Li H.Z., and Yang C.R. Steroids 69 (2004) 111-119
4. González A.G., Darias V., Suarez M.C., and Janssen K. Il Farmaco Ed. Sci. 38 (1983) 3-8
5. Mola-Garate J.L., C. de Magalhaes G., and S.-Romeiro L.A. Quim. Nova 21 (1998) 726-730
6. Mola-Gárate J.L., Suárez-García L., Pérez-Martínez C.S., Iglesias-Arteaga M.A., Coll-Herrera D., and Coll-Manchado F. Synth. Commun. 33 (2003) 1203-1209
7. Marker R.E., and Rohrmann E. J. Am. Chem. Soc. 62 (1940) 76-78
8. Marker R.E., and Rohrmann E. J. Am. Chem. Soc. 62 (1940) 518-520
9. Marker R.E., and Shabica A. J. Am. Chem. Soc. 64 (1942) 813-816
10. Corcoran J.W., and Hirschmann H. J. Am. Chem. Soc. 78 (1956) 2325-2330
11. Anagnostopoulos C.E., and Fieser L.F. J. Am. Chem. Soc. 76 (1954) 532-536
12. Barton D.H.R., Sammes P.G., Taylor M.V., and Werstiuk E. J. Chem. Soc. (C) (1970) 1977-1981
13. Morzycki J.W., and Jastrzebska I. Tetrahedron Lett. 42 (2001) 5989-5991
14. Anulewicz-Ostrowska R., Morzycki J.W., Jastrzebska I., and Wojcik J. J. Org. Chem. 67 (2002) 6916-6924
15. Jastrzebska I., Morzycki J.W., and Trochimowicz U. Tetrahedron Lett. 45 (2004) 1929-1932
16. Jastrzêbska I., and Morzycki J.W. Pol. J. Chem. 79 (2005) 1245-1248
17. Iglesias-Arteaga M.A., Velazquez-Huerta G.A., Mendez-Stivalet J.M., Galano A., and Alvarez-Idaboy R. Arkivoc VI (2005) 109-126
18. Sato Y., and Ikekawa N. J. Org. Chem. 25 (1960) 786-789
19. Sato Y., and Ikekawa N. J. Org. Chem. 25 (1960) 789-791
20. Sato Y., and Ikekawa N. J. Org. Chem. 26 (1961) 5058-5061
21. Meza-Reyes S., Sandoval-Ramírez S., Montiel-Smith S., Hernández-Linares G., Viñas-Bravo O., Martínez-Pascual R., Fernández-Herrera M.A., Vega-Báez J.L., Merino-Montiel P., Santillán R.L., Farfán N., Rincón S., and del Río R.E. Arkivoc VI (2005) 307-320
22. Iglesias-Arteaga M.A., Sandoval-Ramirez J., Mata-Esma M.Y., Viñas-Bravo O., and Bernès S. Tetrahedron Lett. 45 (2004) 4921-4926
23. Stewart J.J.P. J. Comput. Chem. 10 (1989) 209-220
24. Stewart, J. J. P. MOPAC 6.00, QCPE 455, 1990.