The synthesis of 4-hydroxyandrost-4-ene-3,17-dione and other potential aromatase inhibitors

Abstract
We describe novel syntheses of 4-hydroxyandrost-4-ene-3,17-dione (Ia) and related compounds, some containing fluorine. In addition we provide further evidence of the general tendency of 2- and 6-substituted androst-4-ene-3,17-diones to undergo rearrangement reactions, and thus provide new routes to 6-fluoro- and 2,6-difluoro-derivatives. Several of these compounds are potent aromatase inhibitors.