Collect. Czech. Chem. Commun. 1987, 52, 487-492

Oxidation of 3β,28-lupanediol diacetate and lupane with peroxyacetic acid

Jan Sejbal, Jiří Klinot and Alois Vystrčil

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


Lupane triterpenoids are attacked by peroxyacetic acid in position 19. 3β,28-Lupanediol diacetate (I) affords the 18β,19β-epoxy derivative III and the 19β-hydroxy derivative V, lupane (II) gives 18β,19β-epoxylupane (IV); however, the yields are low. Structure of the products III and IV was confirmed by independent preparation from the 20(29)-unsaturated compounds IX and X.