Synthesis of substituted estradiols by the selective aromatization of A-ring of steroidal 19-nor-Δ-4-3-ketones with phenylselenyl halides/hydrogen peroxide

•Synthesis of highly substituted estradiol derivatives.•A-ring aromatization of 6-, 7- and 11-substituted 3-keto-Δ-4 19-nor steroids.•Conventional A-ring aromatization methods failed with these substrates.

A range of 6-, 7-, and 11-substituted estradiols were synthesized by the selective aromatization of the A-ring of 19-nor steroids using phenylselenyl halides followed by oxidation with hydrogen peroxide. Established methods utilizing copper(II) halides failed or have given poor yields with these substrates.

Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slide