REGIOSELECTIVE OXIDATION OF THE HYDROXYL GROUP IN POLYHYDROXYLATED TRITERPENES BY THE INDIRECT ANODIC OXIDATION METHOD

Masayuki YOSHIKAWA; Toshiyuki MURAKAMI; Nobuhiro YAGI; Nobutoshi MURAKAMI; Johji YAMAHARA; Hisashi MATSUDA; Hatsuo MAEDA; Hidenobu OHMORI

doi:10.1248/cpb.45.570

Masayuki YOSHIKAWA, Toshiyuki MURAKAMI, Nobuhiro YAGI, Nobutoshi MURAKAMI, Johji YAMAHARA, Hisashi MATSUDA, Hatsuo MAEDA, Hidenobu OHMORI

Author information

Keywords: indirect anodic oxidation, selective hydroxyl oxidation, polyhydroxylated triterpene, soyasapogenol B, electrochemical reaction, olean-12-en-3-one synthesis

JOURNAL FREE ACCESS

1997 Volume 45 Issue 3 Pages 570-572

DOI https://doi.org/10.1248/cpb.45.570

Details

Abstract

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.

Corresponding author

Register with J-STAGE for free!