Alkaloids Reactivity: DFT Analysis of Selective Demethylation Reactions

All possible demethylation reactions of a diverse family of quaternary alkaloids by means of DFT calculations are here described. We aim to develop a rational model that allows the explanation of the high selectivity observed experimentally and predicts the occurrence of new alkaloid derivatives. To...

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Bibliographic Details
Published in:Journal of organic chemistry 2018-12, Vol.83 (24), p.15101-15109
Main Authors: Larrañaga, Olatz, Miranda, José I, Cossío, Fernando P, Cózar, Abel de
Format: Article
Language:English
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Summary:All possible demethylation reactions of a diverse family of quaternary alkaloids by means of DFT calculations are here described. We aim to develop a rational model that allows the explanation of the high selectivity observed experimentally and predicts the occurrence of new alkaloid derivatives. To this end, we have performed a detailed analysis of the initial reagents and products. In addition, as a proof of concept, an experimentally unknown demethylation reaction of coralyne has been carried out, thus verifying the reliability of the theoretical model presented here.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.8b02364