Synthesis of 19-hydroxysteroids I. New synthesis of 19-hydroxytestosterone

For obtaining 19-hydroxytestosterone from dehydroepiandrosterone a new scheme of synthesis has been developed the key stages of which are the reduction of the 17-keto group to a 17-alcohol, the functionalization of the 19-methyl group via the bromohydrin with the formation of a 6,19-epoxide, the selective hydrolysis of the free -acetoxy group, the conversion of the 3-hydroxy-5-bromo derivative into the ⁴-3-ketone, and the reductive cleavage of the 6,19-epoxide ring.Institute of Bioorganic Chemistry, Belorussian Academy of Sciences, Minsk. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 672–678, November–December, 1992.