Smilagenin Transformation Products Under Lewis Acid Catalysis in Acetic Anhydride and Synthesis of 23-Acetyl-Spirostanols
Juan-Pablo García-Merinos,
Rebeca Yépez,
Claudia M. Ramírez-Lozano
et al.
Abstract:Objective: The present contribution describes a novel approach for obtaining steroid derivatives of the iso-type from sapogenins for drug discovery. Methodology: Diastereomeric 23-acetyl-spirostanols were prepared by acetolysis of smilagenin (4) (25 R) using boron trifluoride diethyl etherate in acetic anhydride followed by treatment of the epimeric epoxycholestene obtained (6 or 9) under basic hydrolysis. Higher regioselectivity was attained in the presence of ZnCl2 in acetic anhydride. Results: Acetolysis of… Show more
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