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Chirality and numbering of substituted tropane alkaloids

Authordc.contributor.authorHumam, Munir 
Authordc.contributor.authorShoul, Tarik 
Authordc.contributor.authorJeannerat, Damien 
Authordc.contributor.authorMuñoz Muñoz, Orlando 
Authordc.contributor.authorChristen, Philippe 
Admission datedc.date.accessioned2018-12-20T14:12:55Z
Available datedc.date.available2018-12-20T14:12:55Z
Publication datedc.date.issued2011
Cita de ítemdc.identifier.citationMolecules, Volumen 16, Issue 9, 2018, Pages 7199-7209
Identifierdc.identifier.issn14203049
Identifierdc.identifier.other10.3390/molecules16097199
Identifierdc.identifier.urihttp://repositorio.uchile.cl/handle/2250/154875
Abstractdc.description.abstractThe strict application of IUPAC rules for the numbering of tropane alkaloids is not always applied by authors and there is hence a lot of confusion in the literature. In most cases, the notation of 3, 6/7-disubstituted derivatives has been chosen arbitrarily, based on NMR and MS data, without taking into account the absolute configuration of these two carbons. This paper discusses the problem and the relevance of CD and NMR to determine molecular configurations. We report on the use of 1H-NMR anisochrony (Δδ) induced by the Mosher's chiral auxiliary reagents (R)-(-)-and (S)-(+)-α-methoxy-α-trifluoromethylphenylacetyl chlorides (MTPA-Cl), to determine the absolute configuration of (3R,6R)-3α-hydroxy-6β- senecioyloxytropane, a disubstituted tropane alkaloid isolated from the aerial parts of Schizanthus grahamii (Solanaceae). These analytical tools should help future works in correctly assigning the configuration of additional 3, 6/7 disubstituted tropane derivatives. © 2011 by The Author
Lenguagedc.language.isoen
Type of licensedc.rightsAttribution-NonCommercial-NoDerivs 3.0 Chile
Link to Licensedc.rights.urihttp://creativecommons.org/licenses/by-nc-nd/3.0/cl/
Sourcedc.sourceMolecules
Keywordsdc.subject(3R,6R)-3α-hydroxy-6β-senecioyloxytropane
Keywordsdc.subjectMolecular configuration
Keywordsdc.subjectMosher's esters
Keywordsdc.subjectSchizanthus
Keywordsdc.subjectTropane alkaloids
Títulodc.titleChirality and numbering of substituted tropane alkaloids
Document typedc.typeArtículo de revista
Catalogueruchile.catalogadorSCOPUS
Indexationuchile.indexArtículo de publicación SCOPUS
uchile.cosechauchile.cosechaSI


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Attribution-NonCommercial-NoDerivs 3.0 Chile
Except where otherwise noted, this item's license is described as Attribution-NonCommercial-NoDerivs 3.0 Chile