Baeyer-Villiger reaction of steroid sapogenins by CF3COOH-H2O2. A short cut to pregnan-3β,16β,20-triol 3-monoacetates

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Abstract

Treatment of steroid sapogenins with H2O2 in CF3COOH for 15 min followed by reflux in CH3OH/H2O afforded good yields of pregnan-3β,16β,20-triol 3-monoacetates. When the hydrolysis step was carried out with KOH in refluxing methanol excellent yields pregnantriols were obtained. The resulting compounds were characterized by their melting points and NMR spectral data. An X-ray diffraction analysis of compound 3a confirmed the proposed structure and provided detailed information about the bond lengths, bond angles and conformation.

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