Copper oxidation chemistry using a 19-iminopyridine-bearing steroidal ligand: (i) C5-C6 olefin difunctionalization and (ii) C1β-hydroxylation/C19-peroxidation (Draft: cdc52a13)

Copper oxidations of a steroid were discovered when a C19-iminopyridine derivative was synthesized and treated with copper and hydrogen peroxide. When the steroid ring had a 5alpha-reduced backbone, the reaction resulted in the hydroxylation and peroxidation at the C1 and C19 positions, respectively. When the steroid ring contained a double bond at the C5-C6 position, an olefin difunctionalization occurred, which involved the incorporation of a hydroxy group and a nitrate ester at C5 and C6, respectively. The paper was published in the journal, Steroids, in 2023 (10.1016/j.steroids.2022.109088). The NMR files are provided.