Reactions of Diels-Alder adducts of a sugar-derived dihydropyranone leading to fused polycyclic compounds
Manipulation of the ketone and alkene functions of cycloadducts 2, 3, and 4, derived from optically active (ee >86%) (S)-2-benzyl-2H-pyran-3(6H)-one (1), led to polycyclic systems having three or four fused rings. Reduction of the carbonyl group of the butadiene adduct (2) took place with low fac...
Guardado en:
| Autor principal: | |
|---|---|
| Otros Autores: | |
| Formato: | Capítulo de libro |
| Lenguaje: | Inglés |
| Publicado: |
2004
|
| Materias: | |
| Acceso en línea: | Registro en Scopus DOI Handle Registro en la Biblioteca Digital |
| Aporte de: | Registro referencial: Solicitar el recurso aquí |
| LEADER | 07214caa a22012617a 4500 | ||
|---|---|---|---|
| 001 | PAPER-4591 | ||
| 003 | AR-BaUEN | ||
| 005 | 20230518203409.0 | ||
| 008 | 190411s2004 xx ||||fo|||| 00| 0 eng|d | ||
| 024 | 7 | |2 scopus |a 2-s2.0-1942453242 | |
| 024 | 7 | |2 cas |a 1,3 butadiene, 106-99-0, 25339-57-5; iodide, 20461-54-5; iodine, 7553-56-2; Alcohols; Carbon, 7440-44-0; Cyclopentanes; Oxygen, 7782-44-7; Polycyclic Compounds | |
| 040 | |a Scopus |b spa |c AR-BaUEN |d AR-BaUEN | ||
| 030 | |a CRBRA | ||
| 100 | 1 | |a Capaccio, C.A.I. | |
| 245 | 1 | 0 | |a Reactions of Diels-Alder adducts of a sugar-derived dihydropyranone leading to fused polycyclic compounds |
| 260 | |c 2004 | ||
| 270 | 1 | 0 | |m Varela, O.; CIHIDECAR-CONICET, Depto. de Quim. Orgánica, Pabellón II, 1428 Buenos Aires, Argentina; email: varela@qo.fcen.uba.ar |
| 506 | |2 openaire |e Política editorial | ||
| 504 | |a Nicolaou, K.C., Snyder, S.A., Montagnon, T., Vassilikogiannakis, G., (2002) Angew. Chem., Int. Ed., 41, pp. 1668-1698 | ||
| 504 | |a Corey, E.J., (2002) Angew. Chem., Int. Ed., 41, pp. 1650-1667 | ||
| 504 | |a Bear, B.R., Sparks, S.M., Shea, K., (2001) Angew. Chem., Int. Ed., 40, pp. 820-849 | ||
| 504 | |a Ciganek, E., (1984) Org. React., 32, pp. 1-374 | ||
| 504 | |a Brieger, G., Bennett, J.N., (1980) Chem. Rev., 80, pp. 63-97 | ||
| 504 | |a Roush, W.R., (1991) Comprehensive Organic Synthesis: Selectivity, Strategy & Efficiency in Modern Organic Chemistry, 5, pp. 513-550. , B.M. Trost, I. Fleming, Paquette L.A. Oxford: Pergamon | ||
| 504 | |a Wu, H.-J., Tsai, S.-H., Chung, W.-S., (1996) Tetrahedron Lett., 37, pp. 8209-8212 | ||
| 504 | |a Essig, M.G., Shafizadeh, F., (1984) Carbohydr. Res., 127, pp. 235-244 | ||
| 504 | |a Fleming, I., Michael, J.P., (1978) J. Chem. Soc., Chem. Commun., pp. 245-247 | ||
| 504 | |a Paquette, L.A., Berk, H.C., Degenhardt, C.R., Ewing, G.D., (1977) J. Am. Chem. Soc., 99, pp. 4764-4772 | ||
| 504 | |a Kato, M., Kageyama, M., Tanaka, R., Kuwahara, K., Yoshikoshi, A., (1975) J. Org. Chem., 40, pp. 1932-1941 | ||
| 504 | |a Konno, H., Ogasawara, K., (1998) Synlett, pp. 1004-1006 | ||
| 504 | |a Konno, H., Hiroya, K., Ogasawara, K., (1997) Tetrahedron Lett., 38, pp. 6023-6026 | ||
| 504 | |a Honzumi, M., Hiroya, K., Taniguchi, T., Ogasawara, K., (1999) J. Chem. Soc., Chem. Commun., pp. 1985-1986 | ||
| 504 | |a Iriarte Capaccio, C.A., Varela, O., (2001) J. Org. Chem., 66, pp. 8859-8866 | ||
| 504 | |a Iriarte Capaccio, C.A., Varela, O., (2002) J. Org. Chem., 67, pp. 7839-7846 | ||
| 504 | |a Tvaroska, I., Bleha, T., (1989) Adv. Carbohydr. Chem. Biochem., 47, pp. 45-123 | ||
| 504 | |a Henbest, H.B., Nicholls, B., (1959) J. Chem. Soc., pp. 221-226 | ||
| 504 | |a Ward, D.D., Shafizadeh, F., (1981) Carbohydr. Res., 95, pp. 155-176 | ||
| 504 | |a Horton, D., Roski, J.P., Norris, P., (1996) J. Org. Chem., 61, pp. 3783-3793 | ||
| 504 | |a Bhaté, P., Horton, D., (1983) Carbohydr. Res., 122, pp. 189-199 | ||
| 504 | |a Horton, D., Roski, J.P., (1992) J. Chem. Soc., Chem. Commun., pp. 759-760 | ||
| 504 | |a Dowle, M.D., Davis, D.I., (1979) Chem. Soc. Rev., 8, pp. 171-197 | ||
| 504 | |a Iriarte Capaccio, C.A., Varela, O., (2003) Tetrahedron Lett., 44, pp. 4023-4026 | ||
| 520 | 3 | |a Manipulation of the ketone and alkene functions of cycloadducts 2, 3, and 4, derived from optically active (ee >86%) (S)-2-benzyl-2H-pyran-3(6H)-one (1), led to polycyclic systems having three or four fused rings. Reduction of the carbonyl group of the butadiene adduct (2) took place with low facial selectivity affording the alcohols 5 and 6 in 1:1.4 ratio. In contrast, a higher diastereoselection was observed for the reduction of the carbonyl of the cyclopentadiene adducts 3 and 4 to give the endo alcohols 10 and 13, respectively. The epoxidation of 6 showed low facial selectivity in the formation 7 and 8, whereas epoxidation of 10 and 13 took place from the exo face of the norbornene system to give spontaneously the polycyclic alcohols 11 and 14 by opening of the epoxide by intramolecular attack of the hydroxyl group of the pyranoid ring. Similarly, addition of iodine to 10 led to the polycyclic iodide 12. © 2004 Elsevier Ltd. All rights reserved. |l eng | |
| 536 | |a Detalles de la financiación: Universidad de Buenos Aires, TX108 | ||
| 536 | |a Detalles de la financiación: Consejo Nacional de Investigaciones Científicas y Técnicas | ||
| 536 | |a Detalles de la financiación: This work was supported by grants from the University of Buenos Aires (Project TX108) and the National Research Council of República Argentina (CONICET). O.V. is a Research Member of CONICET. | ||
| 593 | |a CIHIDECAR-CONICET, Depto. de Quim. Orgánica, Pabellón II, 1428 Buenos Aires, Argentina | ||
| 690 | 1 | 0 | |a CYCLIZATIONS |
| 690 | 1 | 0 | |a CYCLOADDUCTS |
| 690 | 1 | 0 | |a DIELS-ALDER |
| 690 | 1 | 0 | |a DIHYDROPYRANONES |
| 690 | 1 | 0 | |a ALCOHOLS |
| 690 | 1 | 0 | |a IODINE COMPOUNDS |
| 690 | 1 | 0 | |a OLEFINS |
| 690 | 1 | 0 | |a OXIDATION |
| 690 | 1 | 0 | |a POLYCYCLIC AROMATIC HYDROCARBONS |
| 690 | 1 | 0 | |a REDUCTION |
| 690 | 1 | 0 | |a DIASTEREOSELECTION |
| 690 | 1 | 0 | |a INTRAMOLECULAR ATTACKS |
| 690 | 1 | 0 | |a NONBORNENE SYSTEMS |
| 690 | 1 | 0 | |a SUGARS |
| 690 | 1 | 0 | |a 1,3 BUTADIENE |
| 690 | 1 | 0 | |a 2 BENZYL 2H PYRAN 3(6H) ONE |
| 690 | 1 | 0 | |a ALCOHOL DERIVATIVE |
| 690 | 1 | 0 | |a ALKENE |
| 690 | 1 | 0 | |a BENZYL DERIVATIVE |
| 690 | 1 | 0 | |a CARBOHYDRATE DERIVATIVE |
| 690 | 1 | 0 | |a CARBONYL DERIVATIVE |
| 690 | 1 | 0 | |a CYCLOPENTADIENE DERIVATIVE |
| 690 | 1 | 0 | |a DIHYDROPYRANONE |
| 690 | 1 | 0 | |a IODIDE |
| 690 | 1 | 0 | |a IODINE |
| 690 | 1 | 0 | |a KETONE |
| 690 | 1 | 0 | |a POLYCYCLIC HYDROCARBON |
| 690 | 1 | 0 | |a UNCLASSIFIED DRUG |
| 690 | 1 | 0 | |a ARTICLE |
| 690 | 1 | 0 | |a DIELS ALDER REACTION |
| 690 | 1 | 0 | |a EPOXIDATION |
| 690 | 1 | 0 | |a PRIORITY JOURNAL |
| 690 | 1 | 0 | |a REDUCTION |
| 690 | 1 | 0 | |a STEREOCHEMISTRY |
| 690 | 1 | 0 | |a ALCOHOLS |
| 690 | 1 | 0 | |a BIOCHEMISTRY |
| 690 | 1 | 0 | |a CARBOHYDRATE CONFORMATION |
| 690 | 1 | 0 | |a CARBOHYDRATE SEQUENCE |
| 690 | 1 | 0 | |a CHROMATOGRAPHY |
| 690 | 1 | 0 | |a CHROMATOGRAPHY, THIN LAYER |
| 690 | 1 | 0 | |a CYCLOPENTANES |
| 690 | 1 | 0 | |a MAGNETIC RESONANCE SPECTROSCOPY |
| 690 | 1 | 0 | |a MODELS, CHEMICAL |
| 690 | 1 | 0 | |a MOLECULAR SEQUENCE DATA |
| 690 | 1 | 0 | |a OXYGEN |
| 690 | 1 | 0 | |a POLYCYCLIC COMPOUNDS |
| 690 | 1 | 0 | |a SPECTROPHOTOMETRY |
| 690 | 1 | 0 | |a STEREOISOMERISM |
| 690 | 1 | 0 | |a ULTRAVIOLET RAYS |
| 690 | 1 | 0 | |a BETULACEAE |
| 650 | 1 | 7 | |2 spines |a CARBON |
| 700 | 1 | |a Varela, O. | |
| 773 | 0 | |d 2004 |g v. 339 |h pp. 1207-1213 |k n. 6 |p Carbohydr. Res. |x 00086215 |w (AR-BaUEN)CENRE-301 |t Carbohydrate Research | |
| 856 | 4 | 1 | |u https://www.scopus.com/inward/record.uri?eid=2-s2.0-1942453242&doi=10.1016%2fj.carres.2004.01.008&partnerID=40&md5=f7eea4d0041c7376287258fb635901df |y Registro en Scopus |
| 856 | 4 | 0 | |u https://doi.org/10.1016/j.carres.2004.01.008 |y DOI |
| 856 | 4 | 0 | |u https://hdl.handle.net/20.500.12110/paper_00086215_v339_n6_p1207_Capaccio |y Handle |
| 856 | 4 | 0 | |u https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v339_n6_p1207_Capaccio |y Registro en la Biblioteca Digital |
| 961 | |a paper_00086215_v339_n6_p1207_Capaccio |b paper |c PE | ||
| 962 | |a info:eu-repo/semantics/article |a info:ar-repo/semantics/artículo |b info:eu-repo/semantics/publishedVersion | ||
| 963 | |a VARI | ||
| 999 | |c 65544 | ||