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Steviamine, a new class of indolizidine alkaloid [(1R,2S,3R,5R,8aR)-3-hydroxymethyl-5-methyloctahydroindolizine-1,2-diol hydrobromide]

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Author(s): Amber L. Thompson | Agnieszka Michalik | Robert J. Nash | Francis X. Wilson | Renate van Well | Peter Johnson | George W. J. Fleet | Chu-Yi Yu | Xiang-Guo Hu | Richard I. Cooper | David J. Watkin

Journal: Acta Crystallographica Section E
ISSN 1600-5368

Volume: 65;
Issue: 11;
Start page: o2904;
Date: 2009;
Original page

ABSTRACT
X-ray crystallographic analysis of the title hydrobromide salt, C10H20N+·Br−, of (1R,2S,3R,5R,8aR)-3-hydroxymethyl-5-methyloctahydroindolizine-1,2-diol defines the absolute and relative stereochemistry at the five chiral centres in steviamine, a new class of polyhydroxylated indolizidine alkaloid isolated from Stevia rebaudiana (Asteraceae) leaves. In the crystal structure, molecules are linked by intermolecular O—H...Br and N—H...Br hydrogen bonds, forming double chains around the twofold screw axes along the b-axis direction. Intramolecular O—H...O interactions occur.
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