Collect. Czech. Chem. Commun. 1986, 51, 581-592

Isomeric oximes of 30-norlupan-20-one and its derivatives

Alois Vystrčila, Václav Křečeka, Miloš Buděšínskýb and Jiří Protiva

a Department of Chemistry, Charles University, 128 40 Prague 2
b Institute of Organic Chemistry and Biochemistry, Czechoslovak Academy of Sciences, 166 10 Prague 6


30-Norlupan-20-one (Ib) and its derivatives IIb-Vb were converted into 5 : 1-10 :1 mixtures of relatively stable E and Z oximes Ic,d-Vc,d. Beckmann rearrangement of the oxime mixtures (as obtained from the oximation) afforded isomeric amides VIII-XII and XIII-XVI in the ratios 3.5 : 1 to 5 : 1. Oximes Vc,d with the E-ring bridged by a lactone grouping, react with difficulty and the rearrangement was proved only for the Z-isomer Vd.