Collect. Czech. Chem. Commun. 2008, 73, 1825-1834

Synthesis of Fluorinated Steroids Using a Novel Fluorinating Reagent Tetrabutylammonium Difluorodimethylphenylsilicate (TAMPS)

Pavel Herrmanna, Jaroslav Kvíčalab, Vladimír Pouzara and Hana Chodounskáa,*

a Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, v.v.i., Flemingovo nám. 2, 166 10 Prague 6, Czech Republic
b Department of Organic Chemistry, Institute of Chemical Technology, Prague, Technická 5, 166 28 Prague 6, Czech Republic; 


Steroidal 3-fluoroderivatives were prepared from corresponding tosylates using tetrabutylammonium 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.

Keywords: Steroidal fluoroderivatives; Stereoselective fluorination; NMR spectroscopy; SN2 reaction.

References: 12 live references.