Collect. Czech. Chem. Commun. 1990, 55, 766-781

Conformation of ring A in triterpenoid and 4,4-dimethylsteroid 3-ketones. Chemical shifts of methyl protons and lanthanide and benzene induced shifts

Jiří Klinota, Miloš Buděšínskýb and Jarmil Světlýa

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


Chemical shifts of signals due to methyl groups in position 10β (in CDCl3) and 4α and 4β (in C6D6) in 1H NMR spectra of pentacyclic triterpene 3-oxo derivatives (V, VIII, IX, and XII) are suitable for estimation of chair-boat equilibrium in the ring A. Benzene and lanthanide induced shifts of 4α and 4β-methyl protons were also used for this purpose. The results obtained with 2α-methyl-3-ketones (III, X) and 2β-methyl-3-ketones (IV, XI) as the respective chair and boat models agree well with those derived from other physical data (about 40% boat). The same methods were applied to 4,4-dimethylsteroid 3-ketones XV-XVII.