Synthesis of 6α-methyl-16α,17α-cyclohexanoprogesterone via γ-methylenation of 16α,17α-cyclohexanopregn-4-ene-3,20-dione

Article abstract of DOI:10.1007/BF02496229

6-Methylene-16α,17α-cyclohexanopregn-4-ene-3,20-dione 2 has been synthesized by the reaction of Δ⁴-3-ketone 1 with CH₂(OEt)₂ and POCl₃ in the presence of AcONa in 55% yield. Reduction of the product 2 in the presence of 5% Pd/C gives 6α-methyl-16α,17α-cyclohexanoprogesterone 3 in a yield exceeding 70%.