Microwave assisted preparation of C(1)-C(11) oxygen-bridged pregnanes
1,11-Epoxysteroids may be obtained by an intramolecular remote functionalization using Suarez reagent (diacetoxyiodobenzene/I 2) and irradiation with visible light. We have found that photolysis with visible light may be advantageously replaced by microwave irradiation to prepare 1,11-oxygen bridges...
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| Acceso en línea: | http://hdl.handle.net/20.500.12110/paper_0039128X_v76_n13_p1458_Alvarez |
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todo:paper_0039128X_v76_n13_p1458_Alvarez2023-10-03T14:49:30Z Microwave assisted preparation of C(1)-C(11) oxygen-bridged pregnanes Alvarez, L.D. Sonego, J.M. Veleiro, A.S. Burton, G. 1,11-Epoxypregnane Diacetoxyiodobenzene Microwave irradiation Remote functionalization 11alpha hydroxyprogesterone 3beta,20 diacetoxy 1alpha iodo 5alpha pregnan 11alpha ol 3beta,20 diacetoxy 1alpha,11alpha epoxy 4 pregnene 3beta,20 diacetoxy 4 pregnen 11alpha ol 3beta,20 diacetoxy 5a pregnan 11alpha ol oxygen pregnane derivative unclassified drug article light methodology microwave irradiation photolysis reaction time Microwaves Models, Molecular Molecular Conformation Oxygen Pregnanes 1,11-Epoxysteroids may be obtained by an intramolecular remote functionalization using Suarez reagent (diacetoxyiodobenzene/I 2) and irradiation with visible light. We have found that photolysis with visible light may be advantageously replaced by microwave irradiation to prepare 1,11-oxygen bridges resulting in higher yields and shorter reaction times especially in the case of sensitive substrates. Both methodologies were compared on a set of representative 11-α-hydroxypregnanes (3, 8, 10 and 11). © 2011 Elsevier Inc. All rights reserved. Fil:Alvarez, L.D. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Sonego, J.M. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Veleiro, A.S. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Burton, G. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_0039128X_v76_n13_p1458_Alvarez |
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Universidad de Buenos Aires |
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I-28 |
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R-134 |
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Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
| topic |
1,11-Epoxypregnane Diacetoxyiodobenzene Microwave irradiation Remote functionalization 11alpha hydroxyprogesterone 3beta,20 diacetoxy 1alpha iodo 5alpha pregnan 11alpha ol 3beta,20 diacetoxy 1alpha,11alpha epoxy 4 pregnene 3beta,20 diacetoxy 4 pregnen 11alpha ol 3beta,20 diacetoxy 5a pregnan 11alpha ol oxygen pregnane derivative unclassified drug article light methodology microwave irradiation photolysis reaction time Microwaves Models, Molecular Molecular Conformation Oxygen Pregnanes |
| spellingShingle |
1,11-Epoxypregnane Diacetoxyiodobenzene Microwave irradiation Remote functionalization 11alpha hydroxyprogesterone 3beta,20 diacetoxy 1alpha iodo 5alpha pregnan 11alpha ol 3beta,20 diacetoxy 1alpha,11alpha epoxy 4 pregnene 3beta,20 diacetoxy 4 pregnen 11alpha ol 3beta,20 diacetoxy 5a pregnan 11alpha ol oxygen pregnane derivative unclassified drug article light methodology microwave irradiation photolysis reaction time Microwaves Models, Molecular Molecular Conformation Oxygen Pregnanes Alvarez, L.D. Sonego, J.M. Veleiro, A.S. Burton, G. Microwave assisted preparation of C(1)-C(11) oxygen-bridged pregnanes |
| topic_facet |
1,11-Epoxypregnane Diacetoxyiodobenzene Microwave irradiation Remote functionalization 11alpha hydroxyprogesterone 3beta,20 diacetoxy 1alpha iodo 5alpha pregnan 11alpha ol 3beta,20 diacetoxy 1alpha,11alpha epoxy 4 pregnene 3beta,20 diacetoxy 4 pregnen 11alpha ol 3beta,20 diacetoxy 5a pregnan 11alpha ol oxygen pregnane derivative unclassified drug article light methodology microwave irradiation photolysis reaction time Microwaves Models, Molecular Molecular Conformation Oxygen Pregnanes |
| description |
1,11-Epoxysteroids may be obtained by an intramolecular remote functionalization using Suarez reagent (diacetoxyiodobenzene/I 2) and irradiation with visible light. We have found that photolysis with visible light may be advantageously replaced by microwave irradiation to prepare 1,11-oxygen bridges resulting in higher yields and shorter reaction times especially in the case of sensitive substrates. Both methodologies were compared on a set of representative 11-α-hydroxypregnanes (3, 8, 10 and 11). © 2011 Elsevier Inc. All rights reserved. |
| format |
JOUR |
| author |
Alvarez, L.D. Sonego, J.M. Veleiro, A.S. Burton, G. |
| author_facet |
Alvarez, L.D. Sonego, J.M. Veleiro, A.S. Burton, G. |
| author_sort |
Alvarez, L.D. |
| title |
Microwave assisted preparation of C(1)-C(11) oxygen-bridged pregnanes |
| title_short |
Microwave assisted preparation of C(1)-C(11) oxygen-bridged pregnanes |
| title_full |
Microwave assisted preparation of C(1)-C(11) oxygen-bridged pregnanes |
| title_fullStr |
Microwave assisted preparation of C(1)-C(11) oxygen-bridged pregnanes |
| title_full_unstemmed |
Microwave assisted preparation of C(1)-C(11) oxygen-bridged pregnanes |
| title_sort |
microwave assisted preparation of c(1)-c(11) oxygen-bridged pregnanes |
| url |
http://hdl.handle.net/20.500.12110/paper_0039128X_v76_n13_p1458_Alvarez |
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AT alvarezld microwaveassistedpreparationofc1c11oxygenbridgedpregnanes AT sonegojm microwaveassistedpreparationofc1c11oxygenbridgedpregnanes AT veleiroas microwaveassistedpreparationofc1c11oxygenbridgedpregnanes AT burtong microwaveassistedpreparationofc1c11oxygenbridgedpregnanes |
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1807315327401328640 |