Microwave assisted preparation of C1-C11 oxygen-bridged pregnanes

Microwave assisted preparation of C1-C11 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 bridge...

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Bibliographic Details
Published in:Steroids Vol. 76; no. 13; pp. 1458 - 1464
Main Authors: Alvarez, Lautaro D, Sonego, Juan M, Veleiro, Adriana S, Burton, Gerardo
Format: Journal Article
Language:English
Published: United States 11-12-2011
Subjects:
Microwaves
Models, Molecular
Molecular Conformation
Oxygen - chemistry
Pregnanes - chemistry
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Summary: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).
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ISSN:1878-5867
DOI:10.1016/j.steroids.2011.07.016