Photolysis of. alpha.-peracetoxynitriles. 2. A comparison of two synthetic approaches to 18-cyano-20-ketosteroids

RW Freerksen, WE Pabst, ML Raggio…

Index: Freerksen; Pabst; Raggio; Sherman; Wroble; Watt Journal of the American Chemical Society, 1977 , vol. 99, # 5 p. 1536 - 1542

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Citation Number: 23

Abstract

Abstract: A new photochemical reaction was utilized to functionalize unactivated carbon- hydrogen bonds in the C-I8 angular methyl group in steroids. The photolysis of 20- peracetoxy-20-cyanosteroids derived from 17-ketosteroids furnished I 8-cyano-20- ketosteroids, For example. the following sequence of reactions was applied to 3P- hydroxyandrost-5-en-I7-one (1 I):(I) protection of the hydroxyl group in 11 using ...

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