Unknown

Dataset Information

0

(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

altmetric image

Publications

(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]

Similar Datasets

| S-EPMC2960798 | biostudies-other
| S-EPMC2960819 | biostudies-other
| S-EPMC2971911 | biostudies-literature
| S-EPMC3200922 | biostudies-literature
| S-EPMC2915019 | biostudies-literature
| S-EPMC3343962 | biostudies-literature
| S-EPMC3885019 | biostudies-literature
| S-EPMC3254557 | biostudies-literature
| S-EPMC3152090 | biostudies-literature
| S-EPMC2960053 | biostudies-literature