Kim W J, Kim J H, Shim S C
Steroids. 1984 May;43(5):491-7. doi: 10.1016/s0039-128x(84)90120-x.
3 alpha-Hydroxy-5 alpha-pregna-9(11),16-diene-20-one (6) was synthesized for the first time from the commercially available 16,17 alpha-epoxy-3 beta-hydroxy-5-pregnen-20-one(1) in several steps. The key step involves a remote chlorination reaction utilizing m-iodobenzoate group as a free-radical guide.