Steroid Transformations 129 



Progesterone (XI), 

 Desoxycorticosterone (XVI) ■ 



xxni 



l,4-Androstadiene-3, 17-dione 



Pyrolysis 



HO' 



XXIV 

 Estrone 



DEHYDROGENATION OF RING A AND CLEAVAGE OF THE 

 SIDE CHAIN AND RING D 



Fried and co-workers (6) have also found that proges- 

 terone (XI), Reichstein's compound S (XIII), and testo- 

 sterone (XXV) can be converted to 1-dehydrotestololactone 

 (XXVI) by Cylindrocarpon radicola. (Compound XXVI 

 can then be converted to Westerfeld's lactone (XXVII) by 

 pyrolysis.) 



OXIDATION OF NUCLEAR HYDROXYL GROUPS 



The original work of Mamoli and Vercellone (14) showed 

 that a nuclear hydroxyl group such as is present in 3P- 



