Oxidation Reactions in 9a-Halosteroids by Jones Reagent

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1. Verfasser: Sara Montiel Smith
Format: Artículo científico
Sprache:en
Veröffentlicht: Sociedad Química de México 2007
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author Sara Montiel Smith
author_facet Sara Montiel Smith
contents Oxidation Reactions in 9a-Halosteroids by Jones Reagent Sara Montiel Smith Mayra Reyes Moreno Ariadna Fuente Hernández José A. Ruiz García Yoanna M. Álvarez Ginarte Hermán Vélez Castro Anaís Fernández Villalobo Socorro Meza Reyes Jesús Sandoval Ramírez Multidisciplinaria (Ciencias Naturales y Exactas) Oxidation androstane stereochemistry anabolic activity Current investigations guided to searching androstanederivatives with potential anabolic activity, weakly androgenic onedirected us to synthesize 3b,11b-dihydroxy-9a-halo-5a-androstane-17-ones (4a-c). These compounds were oxidized by Jones’ Reagentat 0oC obtaining a selective oxidation of the equatorial 3b-hydroxylgroup. This behaviour could be explained by the high steric hindranceat the 11b-position, increased by the strong inductive effect of thehalogen atom at C-9a over the electronic density of the H-11a. 2007 artículo científico 1870-249X https://www.redalyc.org/articulo.oa?id=47551412 en http://www.redalyc.org/revista.oa?id=475 Journal of the Mexican Chemical Society application/pdf Sociedad Química de México Journal of the Mexican Chemical Society (México) Num.4 Vol.51
format Artículo científico
id redalyc_47551412
institution Redalyc
language en
publishDate 2007
publisher Sociedad Química de México
spellingShingle Oxidation Reactions in 9a-Halosteroids by Jones Reagent
Sara Montiel Smith
Multidisciplinaria (Ciencias Naturales y Exactas)
Oxidation
androstane
stereochemistry
anabolic activity
Oxidation Reactions in 9a-Halosteroids by Jones Reagent Sara Montiel Smith Mayra Reyes Moreno Ariadna Fuente Hernández José A. Ruiz García Yoanna M. Álvarez Ginarte Hermán Vélez Castro Anaís Fernández Villalobo Socorro Meza Reyes Jesús Sandoval Ramírez Multidisciplinaria (Ciencias Naturales y Exactas) Oxidation androstane stereochemistry anabolic activity Current investigations guided to searching androstanederivatives with potential anabolic activity, weakly androgenic onedirected us to synthesize 3b,11b-dihydroxy-9a-halo-5a-androstane-17-ones (4a-c). These compounds were oxidized by Jones’ Reagentat 0oC obtaining a selective oxidation of the equatorial 3b-hydroxylgroup. This behaviour could be explained by the high steric hindranceat the 11b-position, increased by the strong inductive effect of thehalogen atom at C-9a over the electronic density of the H-11a. 2007 artículo científico 1870-249X https://www.redalyc.org/articulo.oa?id=47551412 en http://www.redalyc.org/revista.oa?id=475 Journal of the Mexican Chemical Society application/pdf Sociedad Química de México Journal of the Mexican Chemical Society (México) Num.4 Vol.51
title Oxidation Reactions in 9a-Halosteroids by Jones Reagent
topic Multidisciplinaria (Ciencias Naturales y Exactas)
Oxidation
androstane
stereochemistry
anabolic activity
url https://www.redalyc.org/articulo.oa?id=47551412