Next Article in Journal
Effect of ASP2151, a Herpesvirus Helicase-Primase Inhibitor, in a Guinea Pig Model of Genital Herpes
Next Article in Special Issue
Evaluation of the Effects of Mitragyna speciosa Alkaloid Extract on Cytochrome P450 Enzymes Using a High Throughput Assay
Previous Article in Journal
Identification of Dehydroxytrichostatin A as a Novel Up-Regulator of the ATP-Binding Cassette Transporter A1 (ABCA1)
Previous Article in Special Issue
The Growth Suppressing Effects of Girinimbine on Hepg2 Involve Induction of Apoptosis and Cell Cycle Arrest
Article

Chirality and Numbering of Substituted Tropane Alkaloids

1
School of Pharmaceutical Sciences, University of Geneva, University of Lausanne, Quai Ernest-Ansermet 30, CH-1211 Geneva 4, Switzerland
2
Department of Organic Chemistry, University of Geneva, Quai Ernest-Ansermet 30, CH-1211 Geneva 4, Switzerland
3
Departamento de Química, Facultad de Ciencias, Universidad de Chile, Casilla 653, Santiago, Chile
*
Author to whom correspondence should be addressed.
Molecules 2011, 16(9), 7199-7209; https://doi.org/10.3390/molecules16097199
Received: 12 July 2011 / Revised: 16 August 2011 / Accepted: 17 August 2011 / Published: 25 August 2011
(This article belongs to the Special Issue Alkaloids: Novel Therapeutic Perspectives)
The 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 (Δd) induced by the Mosher’s chiral auxiliary reagents (R)-(-)- and (S)-(+)-α-methoxy-α-trifluoromethyl-phenylacetyl chlorides (MTPA-Cl), to determine the absolute configuration of (3R,6R)-3α-hydroxy-6b-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. View Full-Text
Keywords: tropane alkaloids; Schizanthus; molecular configuration; Mosher’s esters; (3R,6R)-3α-hydroxy-6b-senecioyloxytropane tropane alkaloids; Schizanthus; molecular configuration; Mosher’s esters; (3R,6R)-3α-hydroxy-6b-senecioyloxytropane
Show Figures

Graphical abstract

MDPI and ACS Style

Humam, M.; Shoul, T.; Jeannerat, D.; Muñoz, O.; Christen, P. Chirality and Numbering of Substituted Tropane Alkaloids. Molecules 2011, 16, 7199-7209. https://doi.org/10.3390/molecules16097199

AMA Style

Humam M, Shoul T, Jeannerat D, Muñoz O, Christen P. Chirality and Numbering of Substituted Tropane Alkaloids. Molecules. 2011; 16(9):7199-7209. https://doi.org/10.3390/molecules16097199

Chicago/Turabian Style

Humam, Munir, Tarik Shoul, Damien Jeannerat, Orlando Muñoz, and Philippe Christen. 2011. "Chirality and Numbering of Substituted Tropane Alkaloids" Molecules 16, no. 9: 7199-7209. https://doi.org/10.3390/molecules16097199

Find Other Styles

Article Access Map by Country/Region

1
Only visits after 24 November 2015 are recorded.
Back to TopTop