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16Alpha-hydroxy-17-keto steroids, 1, 3, and 8, and their 17beta-hydroxy-16-keto isomers, 4, 5, and 9, were transformed into the corresponding 17beta-alkoxy-16-keto derivatives on treatment with trimethylsilyl iodide (TMSI) in the presence of alkyl alcohol in CHCl3 in poor to high yields.

chemical and pharmaceutical bulletin/chemical and pharmaceutical bulletin

Formation of 17.BETA.-Alkoxy-16-keto Steroids by Reaction of 16.ALPHA.-Hydroxy-17-keto and 17.BETA.-Hydroxy-16-keto Steroids with Trimethylsilyl Iodide in the Presence of Alkyl Alcohols.