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Concise catalytic asymmetric total synthesis of biologically active tropane alkaloids
Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, 106 91 Stockholm, Sweden.
Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, 106 91 Stockholm, Sweden.
Mid Sweden University, Faculty of Science, Technology and Media, Department of applied science and design. (Armando Córdova)
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-α,β-unsaturated enals using only two and three column chromatographic purification steps, respectively. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

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
Organic Chemistry
Identifiers
URN: urn:nbn:se:miun:diva-15959DOI: 10.1002/adsc.201100917ISI: 000303495900018Scopus ID: 2-s2.0-84860777813OAI: oai:DiVA.org:miun-15959DiVA: diva2:505797
Available from: 2012-02-25 Created: 2012-02-25 Last updated: 2012-10-23Bibliographically approved

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