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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Detalles Bibliográficos
Autores principales: Alvarez, L.D., Sonego, J.M., Veleiro, A.S., Burton, G.
Formato: JOUR
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: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
Descripción
Sumario: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.

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