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...
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2004
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| Acceso en línea: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v339_n6_p1207_Capaccio http://hdl.handle.net/20.500.12110/paper_00086215_v339_n6_p1207_Capaccio |
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paper:paper_00086215_v339_n6_p1207_Capaccio2023-06-08T14:32:47Z Reactions of Diels-Alder adducts of a sugar-derived dihydropyranone leading to fused polycyclic compounds Varela, Oscar José 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 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. Fil:Varela, O. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. 2004 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v339_n6_p1207_Capaccio http://hdl.handle.net/20.500.12110/paper_00086215_v339_n6_p1207_Capaccio |
| institution |
Universidad de Buenos Aires |
| institution_str |
I-28 |
| repository_str |
R-134 |
| collection |
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
| topic |
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 |
| spellingShingle |
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 Varela, Oscar José Reactions of Diels-Alder adducts of a sugar-derived dihydropyranone leading to fused polycyclic compounds |
| topic_facet |
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 |
| description |
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. |
| author |
Varela, Oscar José |
| author_facet |
Varela, Oscar José |
| author_sort |
Varela, Oscar José |
| title |
Reactions of Diels-Alder adducts of a sugar-derived dihydropyranone leading to fused polycyclic compounds |
| title_short |
Reactions of Diels-Alder adducts of a sugar-derived dihydropyranone leading to fused polycyclic compounds |
| title_full |
Reactions of Diels-Alder adducts of a sugar-derived dihydropyranone leading to fused polycyclic compounds |
| title_fullStr |
Reactions of Diels-Alder adducts of a sugar-derived dihydropyranone leading to fused polycyclic compounds |
| title_full_unstemmed |
Reactions of Diels-Alder adducts of a sugar-derived dihydropyranone leading to fused polycyclic compounds |
| title_sort |
reactions of diels-alder adducts of a sugar-derived dihydropyranone leading to fused polycyclic compounds |
| publishDate |
2004 |
| url |
https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v339_n6_p1207_Capaccio http://hdl.handle.net/20.500.12110/paper_00086215_v339_n6_p1207_Capaccio |
| work_keys_str_mv |
AT varelaoscarjose reactionsofdielsalderadductsofasugarderiveddihydropyranoneleadingtofusedpolycycliccompounds |
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1768545675132272640 |