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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Autores principales: Alvarez, Lautaro Damián, Sonego, Juan Manuel, Veleiro, Adriana Silvia, Burton, Gerardo
Publicado: 2011
Materias:
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
Acceso en línea:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_0039128X_v76_n13_p1458_Alvarez
http://hdl.handle.net/20.500.12110/paper_0039128X_v76_n13_p1458_Alvarez
Aporte de:
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires
id paper:paper_0039128X_v76_n13_p1458_Alvarez
record_format dspace
spelling paper:paper_0039128X_v76_n13_p1458_Alvarez2023-06-08T15:03:20Z Microwave assisted preparation of C(1)-C(11) oxygen-bridged pregnanes Alvarez, Lautaro Damián Sonego, Juan Manuel Veleiro, Adriana Silvia Burton, Gerardo 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. 2011 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_0039128X_v76_n13_p1458_Alvarez http://hdl.handle.net/20.500.12110/paper_0039128X_v76_n13_p1458_Alvarez
institution Universidad de Buenos Aires
institution_str I-28
repository_str R-134
collection 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, Lautaro Damián
Sonego, Juan Manuel
Veleiro, Adriana Silvia
Burton, Gerardo
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.
author Alvarez, Lautaro Damián
Sonego, Juan Manuel
Veleiro, Adriana Silvia
Burton, Gerardo
author_facet Alvarez, Lautaro Damián
Sonego, Juan Manuel
Veleiro, Adriana Silvia
Burton, Gerardo
author_sort Alvarez, Lautaro Damián
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
publishDate 2011
url https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_0039128X_v76_n13_p1458_Alvarez
http://hdl.handle.net/20.500.12110/paper_0039128X_v76_n13_p1458_Alvarez
work_keys_str_mv AT alvarezlautarodamian microwaveassistedpreparationofc1c11oxygenbridgedpregnanes
AT sonegojuanmanuel microwaveassistedpreparationofc1c11oxygenbridgedpregnanes
AT veleiroadrianasilvia microwaveassistedpreparationofc1c11oxygenbridgedpregnanes
AT burtongerardo microwaveassistedpreparationofc1c11oxygenbridgedpregnanes
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