Navegar

Colección

Datos Estadísticas

Artículo

Estamos trabajando para incorporar este artículo al repositorio
Consulte el artículo en la página del editor
Consulte la política de Acceso Abierto del editor

Abstract:

The thermal and Et 2O·BF 3-catalyzed Diels-Alder additions of 2,3-dimethylbutadiene and cyclopentadiene to (2S,6S)-6- acetoxymethyl-2-(2-propyloxy)-2H-pyran-3(6H)-one 1, derived from d-galactose, afforded the corresponding enantiomerically pure tetrahydrobenzopyrones resulting from the addition of the diene to the α or β face of 1. The facial and endo-exo selectivities in the formation of the adducts, and their yields, are influenced by the diene and the reaction conditions employed. In particular, low overall yields were obtained in the Lewis acid-promoted reactions. This was attributed to the presence of a Lewis base (an acetoxymethyl group) in the pyranone 1. Therefore, (2R,6S)-6-methyl-2-(2-propyloxy)-2H-pyran- 3(6H)-one 7, which possesses a C-6 methyl substituent instead of an acetoxymethyl, was prepared from l-fucose and subjected to the Et 2O·BF 3-catalyzed addition of cyclopentadiene. As expected, a good yield (74%) of the corresponding Diels-Alder product was obtained, with excellent β- and endo-diastereoselectivities.

Registro:

Documento: Artículo
Título:Enantiomerically pure Diels-Alder cycloadducts from aldohexose-derived dihydropyranones
Autor:Iriarte Capaccio, C.A.; Varela, O.
Filiación:CIHIDECAR-CONICET, Depto. de Quím. Orgán., Fac. Cie. Exact. Y Nat., Univ. B., Argentina
Palabras clave:1,3 butadiene; 6 acetoxymethyl 2 (2 propyloxy) 2h pyran 3(6h) one; 6 methyl 2 (2 propyloxy) 2h pyran 3(6h) one; aldohexose; alkadiene; cyclopentadiene derivative; galactose; hexose; ketone derivative; Lewis acid; pyran derivative; unclassified drug; addition reaction; article; carbon nuclear magnetic resonance; catalysis; cycloaddition; diastereoisomer; Diels Alder reaction; enantiomer; nuclear magnetic resonance spectroscopy; nuclear Overhauser effect; priority journal; thin layer chromatography; ultraviolet spectroscopy
Año:2004
Volumen:15
Número:19
Página de inicio:3023
Página de fin:3028
DOI: http://dx.doi.org/10.1016/j.tetasy.2004.08.005
Título revista:Tetrahedron Asymmetry
Título revista abreviado:Tetrahedron Asymmetry
ISSN:09574166
CODEN:TASYE
CAS:1,3 butadiene, 106-99-0, 25339-57-5; galactose, 26566-61-0, 50855-33-9, 59-23-4; hexose, 93780-23-5
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_09574166_v15_n19_p3023_IriarteCapaccio

Referencias:

  • Lichtenthaler, F.W., (1992) Modern Synthetic Methods, 6, pp. 273-376. , R. Scheffold VCH Weinheim/New York
  • Lichtenthaler, F.W., (1986) Natural Products Chemistry, pp. 227-254. , Atta-ur-Rahman Springer New York
  • Lichtenthaler, F.W., (2002) Acc. Chem. Res., 35, pp. 728-737
  • Holder, N.L., (1982) Chem. Rev., 82, pp. 287-332
  • Fraser-Reid, B., (1996) Acc. Chem. Res., 29, pp. 57-66
  • Dauben, W.G., Kowalczyk, B.A., Lichtenthaler, F.W., (1990) J. Org. Chem., 55, pp. 2391-2398
  • Ward, D.D., Shafizadeh, F., (1981) Carbohydr. Res., 95, pp. 155-176
  • Bhaté, P., Horton, D., (1983) Carbohydr. Res., 122, pp. 189-199
  • Horton, D., Roski, J.P., Norris, P., (1996) J. Org. Chem., 61, pp. 3783-3793
  • Horton, D., Roski, J.P., (1992) J. Chem. Soc., Chem. Commun., pp. 759-760
  • Iriarte Capaccio, C.A., Varela, O., (2001) J. Org. Chem., 66, pp. 8859-8866
  • Iriarte Capaccio, C.A., Varela, O., (2003) Tetrahedron Lett., 44, pp. 4023-4026
  • Iriarte Capaccio, C.A., Varela, O., (2002) J. Org. Chem., 67, pp. 7839-7846
  • Varela, O., De Fina, G.M., Lederkremer, R.M., (1987) Carbohydr. Res., 167, pp. 187-196
  • De Fina, G.M., Varela, O., Lederkremer, R.M., (1988) Synthesis, pp. 891-893
  • Varela, O., De Fina, G.M., Lederkremer, R.M., (1993) Carbohydr. Res., 246, pp. 371-376
  • Paulsen, H., Koebernick, H., (1976) Tetrahedron Lett., 17, pp. 2297-2300
  • Iriarte Capaccio, C.A., Varela, O., (2000) Tetrahedron: Asymmetry, 11, pp. 4945-4954
  • Zunszain, P.A., Varela, O., (1998) Tetrahedron: Asymmetry, 9, pp. 1269-1276
  • note; Fringuelli, F., Pizzo, F., Taticchi, A., Halls, T.D.J., Wenkert, E., (1982) J. Org. Chem., 47, pp. 5056-5065
  • Alder, K., Stein, G., (1937) Angew. Chem., 50, pp. 510-519
  • Childs, R.F., Mulholland, D.L., Nixon, A., (1982) Can. J. Chem., 60, pp. 801-808
  • Bonnesen, P.V., Puckett, C.L., Honeychuck, R.V., Hersh, W.H., (1989) J. Am. Chem. Soc., 111, pp. 6070-6081
  • Fringuelli, F., Guo, M., Minuti, L., Pizzo, F., Taticchi, A., Wenkert, E., (1989) J. Org. Chem., 54, pp. 710-712
  • Angell, E.C., Fringuelli, F., Guo, M., Minuti, L., Taticchi, A., Wenkert, E., (1988) J. Org. Chem., 53, pp. 4325-4328
  • Corey, E.J., (2002) Angew. Chem., Int. Ed., 41, pp. 1650-1667
  • Nicolaou, K.C., Snyder, S.A., Montagnon, T., Vassilikogiannakis, G., (2002) Angew. Chem., Int. Ed., 41, pp. 1668-1698
  • Moffett, R.B., (1963) Org. Synth. Coll., 4, pp. 238-241

Citas:

---------- APA ----------
Iriarte Capaccio, C.A. & Varela, O. (2004) . Enantiomerically pure Diels-Alder cycloadducts from aldohexose-derived dihydropyranones. Tetrahedron Asymmetry, 15(19), 3023-3028.
http://dx.doi.org/10.1016/j.tetasy.2004.08.005
---------- CHICAGO ----------
Iriarte Capaccio, C.A., Varela, O. "Enantiomerically pure Diels-Alder cycloadducts from aldohexose-derived dihydropyranones" . Tetrahedron Asymmetry 15, no. 19 (2004) : 3023-3028.
http://dx.doi.org/10.1016/j.tetasy.2004.08.005
---------- MLA ----------
Iriarte Capaccio, C.A., Varela, O. "Enantiomerically pure Diels-Alder cycloadducts from aldohexose-derived dihydropyranones" . Tetrahedron Asymmetry, vol. 15, no. 19, 2004, pp. 3023-3028.
http://dx.doi.org/10.1016/j.tetasy.2004.08.005
---------- VANCOUVER ----------
Iriarte Capaccio, C.A., Varela, O. Enantiomerically pure Diels-Alder cycloadducts from aldohexose-derived dihydropyranones. Tetrahedron Asymmetry. 2004;15(19):3023-3028.
http://dx.doi.org/10.1016/j.tetasy.2004.08.005