Absolute Configuration of a New Alkaloid.

Abstract : The tricyclic guanidine alkaloid was isolated from a Madagascar marine sponge Biemna laboutei. Its structure was elucidated by NMR including 2D techniques. The purpose of this work was to assign the absolute stereostructure of this molecule: 7S, 9R, 10R or 7R, 9S, 10S. The conformations were optimized using the density functional method TDwB97XD/6-31+G(d,p) in vacuum and in methanol. Smd continuum model was used to simulate solvent effect. UV and electronic circular dichroism (ECD) spectra were calculated for the most energetically minimum structures at the TD/B97XD/6-31++G(d,p) level. Then these spectra were weighted according to Boltzmann statistics and the results were compared to experimental UV and ECD spectra measured in methanol. The comparison of theoretical and experimental spectra suggested that 7S,9R,10R enantiomer (1a) was present in Biemna laboutei sponge.
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Poster
Conference on Computational Chemistry, Aug 2013, Réduit, Mauritius
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http://hal.univ-reunion.fr/hal-01244062
Contributeur : Anne Bialecki <>
Soumis le : mardi 15 décembre 2015 - 14:31:02
Dernière modification le : jeudi 11 janvier 2018 - 06:14:40

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  • HAL Id : hal-01244062, version 1

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Emmanuelle Gros, Anne Gauvin-Bialecki, Ali Al Mourabit, Bertrand Illien. Absolute Configuration of a New Alkaloid.. Conference on Computational Chemistry, Aug 2013, Réduit, Mauritius. 〈hal-01244062〉

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