A short total synthesis of dihydrothebainone, dihydrocodeinone, and nordihydrocodeinone

摘要

A method of producing morphinan compounds which incorporates double advantages over the prior art, such as the utilization of β, y-unsaturated ketones in place of the α,β-unsaturated ketones previously used. Additionally, in the step where β,γ-unsaturated bromoketones (13 or 14) proceed to 1-bromo-N-formylnordihydrothebainone (morphinan) (17) there are utilized super acids, such as trifluoromethane sulfonic, trifluoroethane sulfonic and mixtures thereof, and also antimony pentafluoride and mixtures of hydrogen fluoride and antimony pentafluoride. Super acids work, whereas the prior art shows that cyclization in the presence of acids, even strong acids, such as sulfuric, phosphoric, do not work.