Enantiomerically pure Diels-Alder cycloadducts from aldohexose-derived dihydropyranones
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 t...
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| Formato: | Capítulo de libro |
| Lenguaje: | Inglés |
| Publicado: |
2004
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| Acceso en línea: | Registro en Scopus DOI Handle Registro en la Biblioteca Digital |
| Aporte de: | Registro referencial: Solicitar el recurso aquí |
| LEADER | 06884caa a22009857a 4500 | ||
|---|---|---|---|
| 001 | PAPER-21165 | ||
| 003 | AR-BaUEN | ||
| 005 | 20230518205235.0 | ||
| 008 | 190411s2004 xx ||||fo|||| 00| 0 eng|d | ||
| 024 | 7 | |2 scopus |a 2-s2.0-5344220278 | |
| 024 | 7 | |2 cas |a 1,3 butadiene, 106-99-0, 25339-57-5; galactose, 26566-61-0, 50855-33-9, 59-23-4; hexose, 93780-23-5 | |
| 040 | |a Scopus |b spa |c AR-BaUEN |d AR-BaUEN | ||
| 030 | |a TASYE | ||
| 100 | 1 | |a Iriarte Capaccio, C.A. | |
| 245 | 1 | 0 | |a Enantiomerically pure Diels-Alder cycloadducts from aldohexose-derived dihydropyranones |
| 260 | |c 2004 | ||
| 270 | 1 | 0 | |m CIHIDECAR-CONICET, Depto. de Quím. Orgán., Fac. Cie. Exact. Y Nat., Univ. B.Argentina; email: varela@qo.fcen.uba.ar |
| 506 | |2 openaire |e Política editorial | ||
| 504 | |a Lichtenthaler, F.W., (1992) Modern Synthetic Methods, 6, pp. 273-376. , R. Scheffold VCH Weinheim/New York | ||
| 504 | |a Lichtenthaler, F.W., (1986) Natural Products Chemistry, pp. 227-254. , Atta-ur-Rahman Springer New York | ||
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| 504 | |a Horton, D., Roski, J.P., (1992) J. Chem. Soc., Chem. Commun., pp. 759-760 | ||
| 504 | |a Iriarte Capaccio, C.A., Varela, O., (2001) J. Org. Chem., 66, pp. 8859-8866 | ||
| 504 | |a Iriarte Capaccio, C.A., Varela, O., (2003) Tetrahedron Lett., 44, pp. 4023-4026 | ||
| 504 | |a Iriarte Capaccio, C.A., Varela, O., (2002) J. Org. Chem., 67, pp. 7839-7846 | ||
| 504 | |a Varela, O., De Fina, G.M., Lederkremer, R.M., (1987) Carbohydr. Res., 167, pp. 187-196 | ||
| 504 | |a De Fina, G.M., Varela, O., Lederkremer, R.M., (1988) Synthesis, pp. 891-893 | ||
| 504 | |a Varela, O., De Fina, G.M., Lederkremer, R.M., (1993) Carbohydr. Res., 246, pp. 371-376 | ||
| 504 | |a Paulsen, H., Koebernick, H., (1976) Tetrahedron Lett., 17, pp. 2297-2300 | ||
| 504 | |a Iriarte Capaccio, C.A., Varela, O., (2000) Tetrahedron: Asymmetry, 11, pp. 4945-4954 | ||
| 504 | |a Zunszain, P.A., Varela, O., (1998) Tetrahedron: Asymmetry, 9, pp. 1269-1276 | ||
| 504 | |a note; Fringuelli, F., Pizzo, F., Taticchi, A., Halls, T.D.J., Wenkert, E., (1982) J. Org. Chem., 47, pp. 5056-5065 | ||
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| 504 | |a Childs, R.F., Mulholland, D.L., Nixon, A., (1982) Can. J. Chem., 60, pp. 801-808 | ||
| 504 | |a Bonnesen, P.V., Puckett, C.L., Honeychuck, R.V., Hersh, W.H., (1989) J. Am. Chem. Soc., 111, pp. 6070-6081 | ||
| 504 | |a Fringuelli, F., Guo, M., Minuti, L., Pizzo, F., Taticchi, A., Wenkert, E., (1989) J. Org. Chem., 54, pp. 710-712 | ||
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| 504 | |a Corey, E.J., (2002) Angew. Chem., Int. Ed., 41, pp. 1650-1667 | ||
| 504 | |a Nicolaou, K.C., Snyder, S.A., Montagnon, T., Vassilikogiannakis, G., (2002) Angew. Chem., Int. Ed., 41, pp. 1668-1698 | ||
| 504 | |a Moffett, R.B., (1963) Org. Synth. Coll., 4, pp. 238-241 | ||
| 520 | 3 | |a 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. |l eng | |
| 536 | |a Detalles de la financiación: Universidad de Buenos Aires, X108 | ||
| 536 | |a Detalles de la financiación: Consejo Nacional de Investigaciones Científicas y Técnicas | ||
| 536 | |a Detalles de la financiación: Research grants from the University of Buenos Aires (Project X108) and from the National Research Council of República Argentina (CONICET) are gratefully acknowledged. O.V. is a research member of CONICET. | ||
| 593 | |a CIHIDECAR-CONICET, Depto. de Quím. Orgán., Fac. Cie. Exact. Y Nat., Univ. B., Argentina | ||
| 690 | 1 | 0 | |a 1,3 BUTADIENE |
| 690 | 1 | 0 | |a 6 ACETOXYMETHYL 2 (2 PROPYLOXY) 2H PYRAN 3(6H) ONE |
| 690 | 1 | 0 | |a 6 METHYL 2 (2 PROPYLOXY) 2H PYRAN 3(6H) ONE |
| 690 | 1 | 0 | |a ALDOHEXOSE |
| 690 | 1 | 0 | |a ALKADIENE |
| 690 | 1 | 0 | |a CYCLOPENTADIENE DERIVATIVE |
| 690 | 1 | 0 | |a GALACTOSE |
| 690 | 1 | 0 | |a HEXOSE |
| 690 | 1 | 0 | |a KETONE DERIVATIVE |
| 690 | 1 | 0 | |a LEWIS ACID |
| 690 | 1 | 0 | |a PYRAN DERIVATIVE |
| 690 | 1 | 0 | |a UNCLASSIFIED DRUG |
| 690 | 1 | 0 | |a ADDITION REACTION |
| 690 | 1 | 0 | |a ARTICLE |
| 690 | 1 | 0 | |a CARBON NUCLEAR MAGNETIC RESONANCE |
| 690 | 1 | 0 | |a CATALYSIS |
| 690 | 1 | 0 | |a CYCLOADDITION |
| 690 | 1 | 0 | |a DIASTEREOISOMER |
| 690 | 1 | 0 | |a DIELS ALDER REACTION |
| 690 | 1 | 0 | |a ENANTIOMER |
| 690 | 1 | 0 | |a NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY |
| 690 | 1 | 0 | |a NUCLEAR OVERHAUSER EFFECT |
| 690 | 1 | 0 | |a PRIORITY JOURNAL |
| 690 | 1 | 0 | |a THIN LAYER CHROMATOGRAPHY |
| 690 | 1 | 0 | |a ULTRAVIOLET SPECTROSCOPY |
| 700 | 1 | |a Varela, O. | |
| 773 | 0 | |d 2004 |g v. 15 |h pp. 3023-3028 |k n. 19 |p Tetrahedron Asymmetry |x 09574166 |w (AR-BaUEN)CENRE-562 |t Tetrahedron Asymmetry | |
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| 856 | 4 | 0 | |u https://doi.org/10.1016/j.tetasy.2004.08.005 |y DOI |
| 856 | 4 | 0 | |u https://hdl.handle.net/20.500.12110/paper_09574166_v15_n19_p3023_IriarteCapaccio |y Handle |
| 856 | 4 | 0 | |u https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_09574166_v15_n19_p3023_IriarteCapaccio |y Registro en la Biblioteca Digital |
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| 999 | |c 82118 | ||