Formation of 17beta-alkoxy-16-keto steroids by reaction of 16alpha-hydroxy-17-keto and 17beta-hydroxy-16-keto steroids with trimethylsilyl iodide in the presence of alkyl alcohols.
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.
Nagaoka
M
M
Tohoku Pharmaceutical University, Aobaku, Sendai, Japan.
Endo
M
M
Numazawa
M
M
D000438:Alcohols / Q000737:chemistry*; D007454:Iodides / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D013055:Spectrophotometry, Infrared; D013256:Steroids / Q000138:chemical synthesis* / Q000737:chemistry; D014297:Trimethylsilyl Compounds / Q000737:chemistry*
D000438:Alcohols; D007454:Iodides; D013256:Steroids; D014297:Trimethylsilyl Compounds