Stereoselective synthesis of the two major metabolites of spironolactone, 3alpha- and 3beta-hydroxy-7alpha-methylthio-17alpha-pregn-4-ene-21,17-carbolactone.
7Alpha-methylthio-3beta-hydroxy-17alpha-pregn-4-ene-21,17-carbolactone and 7alpha-methylthio-3alpha-hydroxy-17alpha-pregn-4-ene-21,17-carbolactone, the two major metabolites of spironolactone, were prepared stereoselectively by exploring different types of reduction reagents. For the 3beta-hydroxyl isomer, the application of NaBH4/CeCl3.7H2O gave the best result while for the 3alpha-hydroxyl isomer, K-selectride seemed to provide the highest stereoselectivity.
Li
Guo
G
Department of Medicinal Chemistry, Virginia Commonwealth University, 410 North 12th Street, P.O. Box 980540, Richmond, VA 23298-0540, USA.
Zhang
Yan
Y
D009682:Magnetic Resonance Spectroscopy; D021241:Spectrometry, Mass, Electrospray Ionization; D013148:Spironolactone / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D013237:Stereoisomerism
D013148:Spironolactone