Synthesis of fluorinated steroids using a novel fluorinating reagent tetrabutylammonium difluorodimethylphenylsilicate (TAMPS)

Article abstract of DOI:10.1135/cccc20081825

Steroidal 3-fluoroderivatives were prepared from corresponding tosylates using tetrabutyl-ammonium difluorodimethylphenylsilicate as fluorinating agent. The reaction was tested on all four possible C-3 and C-5 stereoisomers of cholestane and 17-oxoandrostane skeletons. In this reaction only one isomer was always formed with opposite configuration at C-3 to starting tosylate. The reaction is accompanied by elimination which affords a mixture of corresponding olefines.