(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
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author Neelakantan, Sundar
Parkin, Sean
Crooks, Peter A.
author_facet Neelakantan, Sundar
Parkin, Sean
Crooks, Peter A.
author_sort Neelakantan, Sundar
collection PubMed
description 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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spelling pubmed-29693772010-12-30 (11R)-13-Dimethyl­ammonio-11,13-dihydro-4,5-epoxy­costunolide semifumarate Neelakantan, Sundar Parkin, Sean Crooks, Peter A. Acta Crystallogr Sect E Struct Rep Online Organic Papers 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. International Union of Crystallography 2009-06-13 /pmc/articles/PMC2969377/ /pubmed/21582849 http://dx.doi.org/10.1107/S1600536809021941 Text en © Neelakantan et al. 2009 http://creativecommons.org/licenses/by/2.0/uk/ This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
spellingShingle Organic Papers
Neelakantan, Sundar
Parkin, Sean
Crooks, Peter A.
(11R)-13-Dimethyl­ammonio-11,13-dihydro-4,5-epoxy­costunolide semifumarate
title (11R)-13-Dimethyl­ammonio-11,13-dihydro-4,5-epoxy­costunolide semifumarate
title_full (11R)-13-Dimethyl­ammonio-11,13-dihydro-4,5-epoxy­costunolide semifumarate
title_fullStr (11R)-13-Dimethyl­ammonio-11,13-dihydro-4,5-epoxy­costunolide semifumarate
title_full_unstemmed (11R)-13-Dimethyl­ammonio-11,13-dihydro-4,5-epoxy­costunolide semifumarate
title_short (11R)-13-Dimethyl­ammonio-11,13-dihydro-4,5-epoxy­costunolide semifumarate
title_sort (11r)-13-dimethyl­ammonio-11,13-dihydro-4,5-epoxy­costunolide semifumarate
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2969377/
https://www.ncbi.nlm.nih.gov/pubmed/21582849
http://dx.doi.org/10.1107/S1600536809021941
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AT parkinsean 11r13dimethylammonio1113dihydro45epoxycostunolidesemifumarate
AT crookspetera 11r13dimethylammonio1113dihydro45epoxycostunolidesemifumarate

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