(11R)-13-Dimethyl­ammonio-11,13-dihydro-4,5-epoxy­costunolide semifumarate

Crystals of the title salt, C(17)H(28)NO(3) (+)·C(4)H(3)O(4) (−), were obtained by reacting parthenolide with dimethyl­amine followed by conversion of the amine adduct into a water-soluble fumarate salt. Subsequent crystallization of the fumarate salt from water afforded colorless ortho­rhom­bic cry...

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Detalles Bibliográficos
Autores principales: Neelakantan, Sundar, Parkin, Sean, Crooks, Peter A.
Formato: Texto
Lenguaje:English
Publicado: International Union of Crystallography 2009
Materias:
Organic Papers
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2969377/
https://www.ncbi.nlm.nih.gov/pubmed/21582849
http://dx.doi.org/10.1107/S1600536809021941
Descripción
Sumario:Crystals of the title salt, C(17)H(28)NO(3) (+)·C(4)H(3)O(4) (−), were obtained by reacting parthenolide with dimethyl­amine followed by conversion of the amine adduct into a water-soluble fumarate salt. Subsequent crystallization of the fumarate salt from water afforded colorless ortho­rhom­bic crystals. The amine addition is highly stereospecific yielding exclusively a single diastereomer with R-configuration at the newly formed C-11 chiral carbon. In the crystal, intermolecular O—H⋯O and N—H⋯O hydrogen bonds help to establish the packing.

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