Collect. Czech. Chem. Commun. 1987, 52, 1786-1802

Configuration of natural 9-hydroxyfuroeremophilane, its 9-hydroxy epimer and furanopetasin: NMR and CD studies

Ladislav Novotnýa, Miloš Buděšínskýa, Josef Jizbaa, Juraj Harmathaa, Vít Lukeša, Wolfgang Lindnerb, Rolf Grosserb and Günther Snatzkeb

a Institute of Organic Chemistry and Biochemistry, Czechoslovak Academy of Sciences, 166 10 Prague 6, Czechoslovakia
b Lehrstuhl für Strukturchemie, Ruhr-Universität Bochum, D-4630 Bochum 1, F.R.G.


The conformation and configuration analysis of cis- and trans-furoeremophilanes with hydroxy group in position 9, using 1H NMR and CD spectra, is discussed. Some steroid derivatives were used as models for CD study. A combination of both spectral methods gives complementary results. For natural 9-hydroxyfuroeremophilane the configuration 9β-OH was unequivocally proved and the originally proposed structure of furanopetasin corrected to VII.