title: Synthesis of 18-substituted steroids Part II (1). Improvements in the preparation of 18-hydroxyprogesterone.
abstract: 18-Hydroxyprogesterone is conveniently prepared from 3beta-acetoxypregn-5-en-20beta-ol by a modified route. 3beta-Acetoxy-18-iodopregn-5-en-20-one, obtained by the hypoiodite-photolysis procedure and oxidation, is treated with methanolic silver acetate to give the 18, 20-epoxy-20-methoxy derivative, which crystallises directly without need for chromatography. Hydrolysis of the 3-acetate, and a modified Oppenauer oxidation, gave 18-hydroxy-progesterone in 24% over-all yield.
mesh_terms: D055598:Chemical Phenomena; D002621:Chemistry; D006868:Hydrolysis; D006908:Hydroxyprogesterones / Q000138:chemical synthesis*; D008722:Methods; D010084:Oxidation-Reduction; D010782:Photolysis
chemical_list: D006908:Hydroxyprogesterones