Stereocontrolled Diels - Alder cycloadditions of sugar-derived dihydropyranones with dienes

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2-Acetoxy-3,4-di-O-acetyl-D-arabinal (6), similar to its D-xylo analogue 4, reacted with benzyl alcohol by the tin(IV) chloride-promoted glycosylation to produce optically active (S)-2-benzyloxy-2H-pyran-3(6H)-one (8a). The L-arabinal derivative (5) gave 9a, the dihydropyranone enantiomer of 8a. The...

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Detalles Bibliográficos
Autor principal: Iriarte Capaccio, C.A
Otros Autores: Varela, O.
Formato: Capítulo de libro
Lenguaje:Inglés
Publicado: 2002
Acceso en línea:Registro en Scopus
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Registro en la Biblioteca Digital
Aporte de:Registro referencial: Solicitar el recurso aquí
Biblioteca Central Dr. Luis F. Leloir (FCEN) de Universidad de Buenos Aires
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024 7 |2 cas  |a 1,3 cyclohexadiene, 592-57-4; 2,3 dimethylbutadiene, 513-81-5; Carbohydrates; Pyrones 
040 |a Scopus  |b spa  |c AR-BaUEN  |d AR-BaUEN 
030 |a JOCEA 
100 1 |a Iriarte Capaccio, C.A. 
245 1 0 |a Stereocontrolled Diels - Alder cycloadditions of sugar-derived dihydropyranones with dienes 
260 |c 2002 
270 1 0 |m Varela, O.; Depto. de Quimica Orgánica, Facultad de Cie. Exact. y Naturales, Universidad de Buenos Aires, Pabellon 2-Ciudad Universitaria, 1428 Buenos Aires, Argentina; email: varela@qo.fcen.uba.ar 
506 |2 openaire  |e Política editorial 
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504 |a Iriarte Capaccio, C.A., Varela, O., (2001) J. Org. Chem., 66, p. 8859 
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504 |a Chalmers, A.A., Hall, R.H., (1974) J. Chem. Soc., Perkin Trans. 2, p. 728 
504 |a Ferrier, R.J., Prasad, N., Sankey, G.H., (1968) J. Chem. Soc., 974 
504 |a Vaino, A.R., Szarek, W.A., (2001) Adv. Carbohydr. Chem. Biochem., 56, p. 9 
504 |a Varela, O., De Fina, G.M., Lederkremer, R.M., (1987) Carbohydr. Res., 167, p. 187 
504 |a Alder, K., Stein, G., (1937) Angew. Chem., 50, p. 510 
504 |a Gleiter, R., Bohm, M.C., (1983) Pure Appl. Chem., 55, p. 237 
504 |a Ginsburg, D., (1983) Tetrahedron, 39, p. 2095 
504 |a Fringuelli, F., Guo, M., Minuti, L., Pizzo, F., Taticchi, A., Wenkert, E., (1989) J. Org. Chem., 54, p. 710 
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504 |a Derome, A.E., (1997) Modern NMR Techniques for Chemistry Research, Tetrahedron Organic Chemistry Series, 6, p. 239. , Baldwin J. E., Magnus P. D., Eds.; Pergamon: Oxford 
504 |a Bock, K., Pedersen, C., (1970) Acta Chem. Scand., 24, p. 2465 
520 3 |a 2-Acetoxy-3,4-di-O-acetyl-D-arabinal (6), similar to its D-xylo analogue 4, reacted with benzyl alcohol by the tin(IV) chloride-promoted glycosylation to produce optically active (S)-2-benzyloxy-2H-pyran-3(6H)-one (8a). The L-arabinal derivative (5) gave 9a, the dihydropyranone enantiomer of 8a. These results indicated that the configuration of the C-4 stereocenter in the starting glycal defines the configuration of the new chiral center in the resulting dihydropyranone. The influence of other catalysts (BF3 or iodine) employed for the glycosylation on the optical purity of the dihydropyranone was studied. Enantiomerically pure dihydropyranones 8b and 9c were obtained using chiral alcohols ((R)- and (S)-2-octanol, respectively) as glycosylating agents. Compounds 8a,b and 9a,c proved to be reactive dienophiles in thermal and Lewis acid-promoted Diels - Alder reactions. The addition of 2,3-dimethylbutadiene, cyclopentadiene, and 1,3-cyclohexadiene to the β-pyranones 8a,b led to the corresponding adducts 10a,b, 12a,b, and 16a,b as major products. Enantiomeric cycloadducts were synthesized from the α-pyranones 9a,c. The main products were formed by highly facial-diastereoselective addition of dienes to the pyranone ring, guided by the sterical hindrance of the alkoxy substituent of the C-2 stereocenter. As cycloadditions with cycloalkadienes were also highly endo diastereoselective, these reactions gave access to pure tetrahydrobenzopyranones that carry a multitude of stereogenic centers installed in a predictable way.  |l eng 
593 |a CIHIDECAR-CONICET, Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pabellón 2-Ciudad Universitaria, 1428, Buenos Aires, Argentina 
690 1 0 |a DIASTEREOSELECTIVITY 
690 1 0 |a ENANTIOMERS 
690 1 0 |a ADDITION REACTIONS 
690 1 0 |a ALCOHOLS 
690 1 0 |a CATALYSTS 
690 1 0 |a OLEFINS 
690 1 0 |a STEREOCHEMISTRY 
690 1 0 |a SYNTHESIS (CHEMICAL) 
690 1 0 |a KETONES 
690 1 0 |a 1,3 BUTADIENE DERIVATIVE 
690 1 0 |a 1,3 CYCLOHEXADIENE 
690 1 0 |a 2 ACETOXY 3,4 DI O ACETYL DEXTRO ARABINAL 
690 1 0 |a 2 BENZYLOXY 2H PYRAN 3(6H) ONE 
690 1 0 |a 2,3 DIMETHYLBUTADIENE 
690 1 0 |a ALKADIENE 
690 1 0 |a ARABINOSE DERIVATIVE 
690 1 0 |a CYCLOPENTADIENE DERIVATIVE 
690 1 0 |a DIHYDROPYRANONE DERIVATIVE 
690 1 0 |a PYRAN DERIVATIVE 
690 1 0 |a TETRAHYDROBENZOPYRANONE DERIVATIVE 
690 1 0 |a UNCLASSIFIED DRUG 
690 1 0 |a ARTICLE 
690 1 0 |a CATALYSIS 
690 1 0 |a CHIRALITY 
690 1 0 |a CYCLOADDITION 
690 1 0 |a ENANTIOMER 
690 1 0 |a OPTICS 
690 1 0 |a PREDICTION 
690 1 0 |a PROTEIN GLYCOSYLATION 
690 1 0 |a REACTION ANALYSIS 
690 1 0 |a STEREOCHEMISTRY 
690 1 0 |a STEREOSPECIFICITY 
690 1 0 |a SYNTHESIS 
690 1 0 |a THERMAL ANALYSIS 
690 1 0 |a CARBOHYDRATES 
690 1 0 |a HYDROXYLATION 
690 1 0 |a MOLECULAR STRUCTURE 
690 1 0 |a PYRONES 
690 1 0 |a STEREOISOMERISM 
690 1 0 |a TEMPERATURE 
700 1 |a Varela, O. 
773 0 |d 2002  |g v. 67  |h pp. 7839-7846  |k n. 22  |p J. Org. Chem.  |x 00223263  |w (AR-BaUEN)CENRE-337  |t Journal of Organic Chemistry 
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