SYNTHESIS OF 19-HYDROXYSTEROIDS I. NEW SYNTHESIS OF 19-HYDROXYTESTOSTERONE

Article abstract of DOI:10.1007/BF00630434

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 6β,19-epoxide, the selective hydrolysis of the free β-acetoxy group, the conversion of the 3β-hydroxy-5α-bromo derivative into the Δ⁴-3-ketone, and the reductive cleavage of the 6β,19-epoxide ring.