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

Sundar Neelakantan; Sean Parkin; Peter A. Crooks

doi:10.1107/S1600536809021941

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

Sundar Neelakantan
, Sean Parkin
, Peter A. Crooks

Chemistry

Research output: Contribution to journal › Article › peer-review

2 Scopus citations

Abstract

Crystals of the title salt, C₁₇H₂₈NO ₃+·C₄H₃O₄^-, 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.

Original language	English
Pages (from-to)	o1569
Journal	Acta Crystallographica Section E: Structure Reports Online
Volume	65
Issue number	7
DOIs	https://doi.org/10.1107/S1600536809021941
State	Published - 2009

ASJC Scopus subject areas

General Chemistry
General Materials Science
Condensed Matter Physics

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

abstract = "Crystals of the title salt, C17H28NO 3+·C4H3O4-, 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.",

author = "Sundar Neelakantan and Sean Parkin and Crooks, \{Peter A.\}",

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doi = "10.1107/S1600536809021941",

language = "English",

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TY - JOUR

T1 - (11R)-13-Dimethylammonio-11,13-dihydro-4,5-epoxycostunolide semifumarate

AU - Neelakantan, Sundar

AU - Parkin, Sean

AU - Crooks, Peter A.

PY - 2009

Y1 - 2009

N2 - Crystals of the title salt, C17H28NO 3+·C4H3O4-, 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.

AB - Crystals of the title salt, C17H28NO 3+·C4H3O4-, 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.

UR - https://www.scopus.com/pages/publications/67650812605

UR - https://www.scopus.com/pages/publications/67650812605#tab=citedBy

U2 - 10.1107/S1600536809021941

DO - 10.1107/S1600536809021941

M3 - Article

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AN - SCOPUS:67650812605

SN - 1600-5368

VL - 65

SP - o1569

JO - Acta Crystallographica Section E: Structure Reports Online

JF - Acta Crystallographica Section E: Structure Reports Online

IS - 7

ER -

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

Abstract

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