Abstract
Dehydrogenation of 17β-hydroxy-(4) and 17β-acetoxy-4-fluoro-oestr-4-en-3-one (5) with selenium dioxide gives 4-fluoro-17β-oestradiol (7) and its 17-acetate (8), respectively. The 19-norsteroid intermediates (2) and (3) were obtained by regiospecific 4β-axial electrophilic fluorination of the pyrrolidine enamine of 19-nortestosterone (1) by perchloryl fluoride.
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