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. 2010 Jul 31;66(Pt 8):o2139-40.
doi: 10.1107/S160053681002903X.

3-Oxo-18α-olean-28,13β-olide

R C Santos, R M A Pinto, A Matos Beja, J A R Salvador, J A Paixão

3-Oxo-18α-olean-28,13β-olide

R C Santos et al. Acta Crystallogr Sect E Struct Rep Online. .

Abstract

The title terpene, C(30)H(46)O(3), is a 28,13β-lactone of oleanolic acid prepared with bis-muth trifluoro-methane-sulfonate (OTf), Bi(OTf)(3)·xH(2)O. All rings are trans-fused. The X-ray study shows the inversion of the orientation of 18-H in the lactonization reaction. A quantum chemical ab-initio Roothaan Hartree-Fock calculation of the equilibrium geometry of the isolated mol-ecule gives values for bond lengths and valency angles in close agreement with experimental values. The calculation also reproduces the observed mol-ecular conformation, with puckering parameters that agree well with those determined from the crystallographic study.

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Figures

Fig. 1.
Fig. 1.
Molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. The H atoms are presented as a small spheres of arbitrary radius.
See this image and copyright information in PMC

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