Improved synthesis of 18-hydroxydeoxycorticosterone.
Hypoiodite photolysis of 3beta-acetoxy-5-pragnen-20beta-olgave 3beta-acetoxy-5-pregnene-18,20-lactone in 46% yield. Lithium aluminum hydride reduction of the latter afforded 3beta, 18,20beta-trihydroxy-5-pregnen (91% yield) which, on Oppenauer oxidation, was converted to 18-hydroxyprogesterone (66%). Lead tetraacetate oxidation followed by mild saponification gave 18-hydroxydeoxycorticosterone (58%) yield).
D015070:18-Hydroxydesoxycorticosterone / Q000138:chemical synthesis*; D000085:Acetates; D055598:Chemical Phenomena; D002621:Chemistry; D003900:Desoxycorticosterone / Q000031:analogs & derivatives*; D007783:Lactones; D009682:Magnetic Resonance Spectroscopy; D008722:Methods; D011283:Pregnenes; D013055:Spectrophotometry, Infrared
D015070:18-Hydroxydesoxycorticosterone; D000085:Acetates; D007783:Lactones; D011283:Pregnenes; D003900:Desoxycorticosterone