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  Trapped in misbelief for almost 40 years: Selective synthesis of the four stereoisomers of mefloquine.

Schützenmeister, N., Müller, M., Reinscheid, U. M., Griesinger, C., & Leonov, A. (2013). Trapped in misbelief for almost 40 years: Selective synthesis of the four stereoisomers of mefloquine. Chemistry, 19(51), 17584-17588. doi:10.1002/chem.201303403.

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Item Permalink: http://hdl.handle.net/11858/00-001M-0000-0015-0E93-F Version Permalink: http://hdl.handle.net/11858/00-001M-0000-0027-CB5C-2
Genre: Journal Article

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1900294.pdf (Publisher version), 268KB
 
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 Creators:
Schützenmeister, N.1, Author              
Müller , M., Author
Reinscheid, U. M.1, Author              
Griesinger, C.1, Author              
Leonov, A.1, Author              
Affiliations:
1Department of NMR Based Structural Biology, MPI for biophysical chemistry, Max Planck Society, ou_578567              

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Free keywords: domino reactions; drug design; mefloquine; structure elucidation; total synthesis
 Abstract: Here we report the synthesis of all four stereoisomers of mefloquine. Mefloquine (Lariam) is an important anti-malaria drug that is applied as a racemate of the erythro form. However, the (-)-isomer induces psychosis, while the (+)-enantiomer does not have this undesired side effect. There are six syntheses of which five lead to the wrong enantiomer without the authors of these syntheses noting that they had synthesized the wrong compound. At the same time physical chemistry investigations had assigned the absolute configuration correctly and the last enantioselective synthesis that took these results into account delivered the correct absolute configuration. Since various synthetic approaches failed to provide the correct stereoisomers in previous syntheses, we submit here a synthetic approach with a domino Sonogashira-6-electrocyclisation as key step that confirmed synthetically the correct absolute configuration of all four isomers.

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Language(s): eng - English
 Dates: 2013-11-132013-12-16
 Publication Status: Published in print
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 Rev. Method: Peer
 Identifiers: DOI: 10.1002/chem.201303403
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Title: Chemistry
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Source Genre: Journal
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Pages: - Volume / Issue: 19 (51) Sequence Number: - Start / End Page: 17584 - 17588 Identifier: ISSN: 0947-6539