The absolute configuration of (+)- and (-)-erythro-mefloquine

Michael Müller; Claudia M Orben; Nina Schützenmeister; Manuel Schmidt; Andrei Leonov; Uwe M Reinscheid; Birger Dittrich; Christian Griesinger

doi:10.1002/anie.201300258

The absolute configuration of (+)- and (-)-erythro-mefloquine

Angew Chem Int Ed Engl. 2013 Jun 3;52(23):6047-9. doi: 10.1002/anie.201300258. Epub 2013 Apr 24.

Authors

Michael Müller¹, Claudia M Orben, Nina Schützenmeister, Manuel Schmidt, Andrei Leonov, Uwe M Reinscheid, Birger Dittrich, Christian Griesinger

Affiliation

¹ Max-Planck-Institut für Biophysikalische Chemie, Department of NMR-Based Structural Biology, Am Fassberg 11, 37077 Göttingen, Germany.

PMID: 23616269
DOI: 10.1002/anie.201300258

Abstract

The controversy over the absolute configuration of (+)-erythro-mefloquine, the less psychosis-causing enantiomer of the anti-malarial drug Lariam, has been resolved by Mosher ester crystallization. The configuration determined previously by physical methods is correct, whereas the configuration determined by three enantioselective syntheses is wrong.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Antimalarials / chemistry*
Erythromycin / chemistry*
Mefloquine / chemistry*
Stereoisomerism

Substances

Antimalarials
Erythromycin
Mefloquine