Bismuth(III) Triflate-Catalyzed Direct Conversion of Corticosteroids into Highly Functionalized 17-Ketosteroids by Cleavage of the C17-Dihydroxyacetone Side Chain

The use of bismuth(III) triflate as catalyst for the direct conversion of corticosteroids into highly functionalized 17-ketosteroids by cleavage of the C17-dihydroxyacetone side chain is reported. This catalytic process is very chemoselective, since functionalities of the starting corticosteroids, s...

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Bibliographic Details
Published in:Journal of organic chemistry 2009-11, Vol.74 (21), p.8488-8491
Main Authors: Pinto, Rui M. A, Salvador, Jorge A. R, Le Roux, Christophe, Paixão, José A
Format: Article
Language:English
Subjects:
17-Ketosteroids - chemistry
Acetone - chemistry
Adrenal Cortex Hormones - chemistry
Alicyclic compounds, terpenoids, prostaglandins, steroids
Catalysis
Chemistry
Chromatography, Thin Layer
Exact sciences and technology
Magnetic Resonance Spectroscopy
Mesylates - chemistry
Organic chemistry
Preparations and properties
Spectrometry, Mass, Electrospray Ionization
Steroids
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Summary:The use of bismuth(III) triflate as catalyst for the direct conversion of corticosteroids into highly functionalized 17-ketosteroids by cleavage of the C17-dihydroxyacetone side chain is reported. This catalytic process is very chemoselective, since functionalities of the starting corticosteroids, such as Δ4-3-keto, Δ1,4-3-keto, 11β-hydroxyl, and 9β,11β-epoxide, remained intact.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo9018478