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Structure and absolute configuration of 3-alkylpiperidine alkaloids from an Indonesian sponge of the genus Halichondria |
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| Authors: | I Wayan Mudianta Peter L Katavic Patricia Y Hayes Murray HG Munro Mary J Garson |
| Institution: | a School of Chemistry and Molecular Biosciences, The University of Queensland, Brisbane, QLD 4072, Australia b Department of Analytical Chemistry, Faculty of Mathematics and Natural Sciences, Ganesha University of Education, Bali, Indonesia c Centre for Magnetic Resonance, The University of Queensland, Brisbane, QLD 4072, Australia d Research School of Chemistry, Institute of Advanced Studies, The Australian National University, Canberra, ACT 0200, Australia e Department of Chemistry, University of Canterbury, Private Bag 4800, Christchurch, New Zealand |
| 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. |
| Keywords: | Sponge 3-Alkylpiperidine N-Oxide X-ray analysis Absolute configuration NMR Biosynthesis Halichondria |
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