| Transformations of 3-hydroxy steroids with Lewis and anhydrous protic acids. The case of pregn-4-en-3β,17α,20β-triol. | |
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MedLine Citation:
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PMID: 21599858 Owner: NLM Status: Publisher |
Abstract/OtherAbstract:
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The acid-catalyzed dehydration is one of the most important processes that transforms 3-hydroxy steroids into their corresponding unsaturated derivatives. This reaction is of great importance because it can produce molecules that play a key role in the understanding of the natural metabolism of steroids. Sterol dehydration is generally performed with aqueous acidic systems and the treatment often affords low yields of the desired compounds and/or complex mixtures of by-products. In this paper we report the results obtained from the study of the structural and stereochemical effects of the acid-induced reaction of pregn-4-en-3β,17α,20β-triol in anhydrous systems. In particular, the treatment of this trihydroxy steroid model with Lewis acids leads to the corresponding Δ(3,5) -steradiene as the only product and in very high yields. With Lewis acids no modifications of the 1,2-diol function on the D-ring is observed, even when the reactions are performed at high temperatures. Protic acid catalysis in non-aqueous organic solvents causes the formation of an epimeric mixture of the corresponding Δ(3,5) -steradiene derivatives by a partial stereochemical inversion of the asymmetric C-17. The reactivity of the 17α,20β-diolic residue is also evaluated by exposing pregn-4-en-3β,17α,20β-triol and the corresponding Δ(3,5) -steradiene to the prolonged action of anhydrous protic acid systems under thermal conditions. |
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Authors:
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Rosaria De Marco; Antonella Leggio; Angelo Liguori; Francesca Perri; Carlo Siciliano |
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Publication Detail:
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Type: JOURNAL ARTICLE Date: 2011-5-20 |
Journal Detail:
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Title: Chemical biology & drug design Volume: - ISSN: 1747-0285 ISO Abbreviation: - Publication Date: 2011 May |
Date Detail:
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Created Date: 2011-5-23 Completed Date: - Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 101262549 Medline TA: Chem Biol Drug Des Country: - |
Other Details:
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Languages: ENG Pagination: - Citation Subset: - |
Copyright Information:
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© 2011 John Wiley & Sons A/S. |
Affiliation:
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Dipartimento di Scienze Farmaceutiche, Università della Calabria, Edificio Polifunzionale I-87036 Arcavacata di Rende (CS), Italy. |
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From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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