Collect. Czech. Chem. Commun. 1994, 59, 1420-1429

Preparation of 2,3-Secodiacids of the Lupane Series

Magdalena Endová, Eva Klinotová, Jan Sejbal, Bohumil Máca, Jiří Klinot and Jiří Protiva

Department of Organic Chemistry, Charles University, 128 40 Prague 2, Czech Republic


2,3-Seco-2,3-diacids of the 28-hydroxy-20(29)-lupene and 28-hydroxylupane series (VIIa and VIIb, respectively) and their derivatives VIII - XIV were prepared from 28-acetoxy-20(29)-lupen-3-one (IIIa) and 28-acetoxy-3-lupanone (IIIb), respectively, by oxidation to diosphenols Va and Vb and subsequent oxidative cleavage of the C(2)-C(3) bond.