Tetrahedron letters

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

BS Chhikara, R Chandra, V Tandon

Index: Chhikara, Bhupender S.; Chandra, Ramesh; Tandon, Vibha Tetrahedron Letters, 2004 , vol. 45, # 41 p. 7585 - 7588

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Citation Number: 35

Abstract

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 17α-methylandrostan-3β, 17β-diol (). At ambient temperature oxidation of with IBX gave mestanolone () in good yield and with an increased stoichiometric amount of IBX, oxidation adjacent to the carbonyl functionality (α, β-unsaturation) occurred to give ...