Synthesis of 11α-hydroxyprogesterone haptens

Article abstract of DOI:10.1016/0039-128X(89)90063-9

C-4 and C-6 bridged haptens of 11α-hydroxyprogesterone, an anti-androgen, were respectively synthesized via 4,5 and 5α,6α epoxide ring openings using 3-mercaptopropanoic acid.Substitution of 6-bromo derivative of progesterone using the same reagent unexpectedly afforded a C-4 substituted product instead of the normal C-6 substituted product previously reported in the literature.