Structure and absolute configuration of 3-alkylpiperidine alkaloids from an Indonesian sponge of the genus Halichondria

Mudianta, IW, Katavic, PL, Lambert, LK, Hayes, PY, Banwell, MG, Munro, MHG, Bernhardt, PV and Garson, MJ (2010) Structure and absolute configuration of 3-alkylpiperidine alkaloids from an Indonesian sponge of the genus Halichondria. Tetrahedron, 66 14: 2752-2760. doi:10.1016/j.tet.2010.01.068


Author Mudianta, IW
Katavic, PL
Lambert, LK
Hayes, PY
Banwell, MG
Munro, MHG
Bernhardt, PV
Garson, MJ
Title Structure and absolute configuration of 3-alkylpiperidine alkaloids from an Indonesian sponge of the genus Halichondria
Formatted title
Structure and absolute configuration of 3-alkylpiperidine alkaloids from an Indonesian sponge of the genus Halichondria
Journal name Tetrahedron   Check publisher's open access policy
ISSN 0040-4020
1464-5416
Publication date 2010-04
Sub-type Article (original research)
DOI 10.1016/j.tet.2010.01.068
Volume 66
Issue 14
Start page 2752
End page 2760
Total pages 9
Place of publication Oxford, United Kingdom
Publisher Pergamon
Collection year 2011
Language eng
Formatted abstract
Chemical analysis of an Indonesian sponge sample has provided three new 3-alkylpiperidine alkaloids, tetradehydrohaliclonacyclamine A, its mono-N-oxide derivative, and a 2-epi isomer. The absolute structure of tetradehydrohaliclonacyclamine A has been established by X-ray crystallography from anomalous dispersion effects using Cu radiation, which determined that the absolute configuration is 2S, 3S, 7S, 9S while an HPLC study revealed that the alkaloid is enantiomerically pure. © 2010 Elsevier Ltd. All rights reserved.
Keyword Sponge
3-Alkylpiperidine
N-Oxide
X-ray analysis
Absolute configuration
Q-Index Code C1
Q-Index Status Confirmed Code
Institutional Status UQ

Document type: Journal Article
Sub-type: Article (original research)
Collections: Official 2011 Collection
School of Chemistry and Molecular Biosciences
Centre for Advanced Imaging Publications
 
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Created: Sun, 25 Apr 2010, 00:00:08 EST