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International Union of Crystallography, Acta Crystallographica Section E: Structure Reports Online, 8(66), p. o2139-o2140, 2010

DOI: 10.1107/s160053681002903x

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3-Oxo-18α-olean-28,13β-olide

This paper is made freely available by the publisher.
This paper is made freely available by the publisher.

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Abstract

The title terpene, C30H46O3, is a 28,13β-lactone of oleanolic acid prepared with bis­muth trifluoro­methane­sulfonate (OTf), Bi(OTf)3·xH2O. 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 mol­ecule gives values for bond lengths and valency angles in close agreement with experimental values. The calculation also reproduces the observed mol­ecular conformation, with puckering parameters that agree well with those determined from the crystallographic study.