Studies on Triterpenoid Corticomimetics (V) - Oxidation of Presenegenin with Chromium Trioxide-Acetic Acid to Yield 11-Keto and 12-Keto Derivatives

Oxidation of presenegenin dimethyl ester triacetate with chromium trioxide in acetic acid yielded two compounds, 11-ketone (IV) and 12-ketone (IV) derivatives. The latter was a main product. On mild alkaline hydrolysis, IV afforded 11-keto-presenegenin dimethyl ester (V), mp 232-$234^{\circ}$, $C_{32}H_{48}O_{8}$, whereas VI did 12-keto-presenegenin dimethyl ester 12, 27-hemiketal (VIII), mp 240-$242^{\circ}$, $C_{32}H_{50}O_{8}$.