IBX in an ionic liquid:: eco-friendly oxidation of 17α-methylandrostan-3β,17β-diol, an intermediate in the synthesis of anabolic oxandrolone

被引：24

作者：

Chhikara, BS ^{[1
]}

Chandra, R ^{[1
]}

Tandon, V ^{[1
]}

机构：

[1] Univ Delhi, Dr BR Ambedkar Ctr Biomed Res, Med Chem Res Lab, Delhi, India

来源：

TETRAHEDRON LETTERS | 2004年 / 45卷 / 41期

关键词：

steroid; oxidation; IBX; mestanolone; dehydrogenation; oxandrolone; ionic liquid; bmim][Br;

D O I：

10.1016/j.tetlet.2004.08.127

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An easily available hypervalent iodine(V) reagent, 2-iodoxybenzoic acid (IBX) immobilized in the ionic liquid [bmim][Br] was found to be an efficient and eco-friendly protocol for the oxidation of 17alpha-methylandrostan-3beta,17beta-diol (1). At ambient temperature oxidation of 1 with lBX gave mestanolone (2) in good yield and with an increased stoichiometric amount of IBX, oxidation adjacent to the carbonyl functionality (alpha,beta-unsaturation) occurred to give dehydrogenated 17 beta-hydroxy- 17alpha-methyl-Delta'-and rosten-3-one (3) as the major product in a one-pot reaction, The product is easily obtained by extraction with diethyl ether and evaporation of the solvent. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：7585 / 7588

页数：4

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