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Concise catalytic asymmetric total synthesis of biologically active tropane alkaloids
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
2012 (English)In: Advanced Synthesis and Catalysis, ISSN 1615-4150, E-ISSN 1615-4169, Vol. 354, no 7, 1363-1372 p.Article in journal (Refereed) Published
Abstract [en]

A general strategy for the total asymmetric synthesis of valuable tropane alkaloids by catalytic stereoselective transformations is disclosed. The power of this approach is exemplified by the concise catalytic enantioselective total syntheses of (+)-methylecgonine, (-)-cocaine and (+)-cocaine as well as the first catalytic asymmetric total syntheses of a cocaine C-1 derivative and (+)-ferruginine starting from 5-oxo-protected-a,beta-unsaturated enals using only two and three column chromatographic purification steps, respectively.

Place, publisher, year, edition, pages
2012. Vol. 354, no 7, 1363-1372 p.
Keyword [en]
asymmetric catalysis, cocaine, cycloadditions, ferruginine, multi-component reactions, stereoselectivity, tandem reactions
National Category
Chemical Sciences
Identifiers
URN: urn:nbn:se:su:diva-80063DOI: 10.1002/adsc.201100917ISI: 000303495900018OAI: oai:DiVA.org:su-80063DiVA: diva2:557254
Funder
Swedish Research Council
Note

AuthorCount:3;

Available from: 2012-09-27 Created: 2012-09-12 Last updated: 2017-12-07Bibliographically approved

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