New way to digitoxigenin from 3β-acetoxy-5-androsten-17-one. Stereoselective free radical substitution of iodide atom by nitrile group as a key step

…, MM Kabat, M Masnyk, W Wojciechowska…

Index: Daniewski, Andrzej Robert; Kabat, Marek Michal; Masnyk, Marek; Wojciechowska, Wanda; Wicha, Jerzy Collection of Czechoslovak Chemical Communications, 1991 , vol. 56, # 5 p. 1064 - 1069

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Citation Number: 6

Abstract

Abstract Digitoxigenin (I) was obtained from 17-oxoandrost-5-en-3β-yl acetate (III) using, as a key step, free radical stereoselective substitution of an iodine atom in VI by a nitrile group. Transformation of the nitrile group at C-17 into a pregnane side chain or a butenolide lactone ring took place without isomerization at C-17.