Abstract
The synthesis of analogs of 6,6-difluoronorethindrone (la) is reported. The new compounds, each of which are potent oral progestational agents, are ( )-6,6-difluoronorgestrel (lb), 17 beta-hydroxy-6,6-difluoro-17alpha-propadienyl-4-estren-3-one (lc), 17beta-hydroxy-6,6-difluoro-17alpha-(1-propynyl)-4-estren-3-one (ld), and 17 beta-hydroxy-6,6-difluoro-17alpha-(3,3,3-trifluoropropynyl)-4-estren-3-o ne (le). The 6,6-gem-difluoro group is an important means for enhancing the progestational activity of parent compounds. Compounds lc,ld, and le were prepared from a common precursor, 6,6-difluoro-4-estrene-3,17-dione 3-ethylene ketal. The findings indicate that 6,6-difluoro steroids are stable towards a variety of reagents. The experimental procedures are summarized.
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