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Abstract:

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.

Registro:

Documento: Artículo
Título:Reactions of Diels-Alder adducts of a sugar-derived dihydropyranone leading to fused polycyclic compounds
Autor:Capaccio, C.A.I.; Varela, O.
Filiación:CIHIDECAR-CONICET, Depto. de Quim. Orgánica, Pabellón II, 1428 Buenos Aires, Argentina
Palabras clave:Cyclizations; Cycloadducts; Diels-Alder; Dihydropyranones; Alcohols; Iodine compounds; Olefins; Oxidation; Polycyclic aromatic hydrocarbons; Reduction; Diastereoselection; Intramolecular attacks; Nonbornene systems; Sugars; 1,3 butadiene; 2 benzyl 2h pyran 3(6h) one; alcohol derivative; alkene; benzyl derivative; carbohydrate derivative; carbonyl derivative; cyclopentadiene derivative; dihydropyranone; iodide; iodine; ketone; polycyclic hydrocarbon; unclassified drug; article; Diels Alder reaction; epoxidation; priority journal; reduction; stereochemistry; Alcohols; Biochemistry; Carbohydrate Conformation; Carbohydrate Sequence; Carbon; Chromatography; Chromatography, Thin Layer; Cyclopentanes; Magnetic Resonance Spectroscopy; Models, Chemical; Molecular Sequence Data; Oxygen; Polycyclic Compounds; Spectrophotometry; Stereoisomerism; Ultraviolet Rays; Betulaceae
Año:2004
Volumen:339
Número:6
Página de inicio:1207
Página de fin:1213
DOI: http://dx.doi.org/10.1016/j.carres.2004.01.008
Título revista:Carbohydrate Research
Título revista abreviado:Carbohydr. Res.
ISSN:00086215
CODEN:CRBRA
CAS: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
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v339_n6_p1207_Capaccio

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Citas:

---------- APA ----------
Capaccio, C.A.I. & Varela, O. (2004) . Reactions of Diels-Alder adducts of a sugar-derived dihydropyranone leading to fused polycyclic compounds. Carbohydrate Research, 339(6), 1207-1213.
http://dx.doi.org/10.1016/j.carres.2004.01.008
---------- CHICAGO ----------
Capaccio, C.A.I., Varela, O. "Reactions of Diels-Alder adducts of a sugar-derived dihydropyranone leading to fused polycyclic compounds" . Carbohydrate Research 339, no. 6 (2004) : 1207-1213.
http://dx.doi.org/10.1016/j.carres.2004.01.008
---------- MLA ----------
Capaccio, C.A.I., Varela, O. "Reactions of Diels-Alder adducts of a sugar-derived dihydropyranone leading to fused polycyclic compounds" . Carbohydrate Research, vol. 339, no. 6, 2004, pp. 1207-1213.
http://dx.doi.org/10.1016/j.carres.2004.01.008
---------- VANCOUVER ----------
Capaccio, C.A.I., Varela, O. Reactions of Diels-Alder adducts of a sugar-derived dihydropyranone leading to fused polycyclic compounds. Carbohydr. Res. 2004;339(6):1207-1213.
http://dx.doi.org/10.1016/j.carres.2004.01.008