In this report we communicate recent results from our investigations w
ith ansa-steroids. Following a detailed inspection of the stereoselect
ivity of epoxidations, a highly regioselective Baeyer-Villiger oxidati
on to form lactones was developed. After deciding on the proper starti
ng material, we were also quite successful with the Birch reduction of
the aromatic ring to generate cyclohexadienes. Efforts to open the fi
ve-membered ring via autoxidation and fragmentation met with failure.