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(11R)-13-Dimethyl-ammonio-11,13-dihydro-4,5-epoxy-costunolide semifumarate.

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

SUBMITTER: Neelakantan S

PROVIDER: S-EPMC2969377 | biostudies-literature | 2009 Jun

REPOSITORIES: biostudies-literature

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(11R)-13-Dimethyl-ammonio-11,13-dihydro-4,5-epoxy-costunolide semifumarate.

Neelakantan Sundar S Parkin Sean S Crooks Peter A PA

Acta crystallographica. Section E, Structure reports online 20090613 Pt 7

Crystals of the title salt, C(17)H(28)NO(3) (+)·C(4)H(3)O(4) (-), were obtained by reacting parthenolide with dimethyl-amine followed by conversion of the amine adduct into a water-soluble fumarate salt. Subsequent crystallization of the fumarate salt from water afforded colorless ortho-rhom-bic 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⋯ ...[more]

PMID: 21582849

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