Regioselective oxidation of the hydroxyl group in polyhydroxylated triterpenes by the indirect anodic oxidation method

Article abstract of DOI:10.1248/cpb.45.570

Indirect anodic oxidation of soyasapogenol B (3β,22β,24- trihydroxyolean-12-ene) was carried out using KI as a mediator in t-BuOH- H₂O solution, so that the 3-ketone derivative was obtained as the only oxidation product in a favorable yield. As a result of application to various polyhydroxylated triterpenes, selective electrochemical oxidation was shown to occur in the C-3 hydroxyl group of the polyhydroxyl triterpenes with the C-24 hydroxyl group. The reaction pathway is discussed.

Full text of DOI:10.1248/cpb.45.570

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