Synthesis and photolysis of doxyl derivatives of 5β‐androstan‐3‐ones

In an unsuccessful attempt to effect remote functionalization at C9, 4,4‐dimethyloxazolidine‐N‐oxyl (doxyl) derivatives at C3 of 5β‐androstan‐3,17‐dione and 5β‐androstan‐17β‐ol‐3‐one were prepared and photolyzed. The former doxyl yielded its C13 stereoisomer; the latter was converted very slowly to intractable material.