3-Oxo-18α-olean-28,13β-olide

The title terpene, C(30)H(46)O(3), is a 28,13β-lactone of oleanolic acid prepared with bis­muth trifluoro­methane­sulfonate (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...

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Detalles Bibliográficos
Autores principales: Santos, R. C., Pinto, R. M. A., Matos Beja, A., Salvador, J. A. R., Paixão, J. A.
Formato: Texto
Lenguaje:English
Publicado: International Union of Crystallography 2010
Materias:
Organic Papers
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3007419/
https://www.ncbi.nlm.nih.gov/pubmed/21588427
http://dx.doi.org/10.1107/S160053681002903X
Descripción
Sumario:The title terpene, C(30)H(46)O(3), is a 28,13β-lactone of oleanolic acid prepared with bis­muth trifluoro­methane­sulfonate (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 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.

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