Journal article

Concise catalytic asymmetric total synthesis of biologically active tropane alkaloids

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Author list: Córdova, Armando

Publication year: 2012

Start page: 1363

End page: 1372

Number of pages: 10

ISSN: 1615-4150

DOI: http://dx.doi.org/10.1002/adsc.201100917

View additional information: View in Web of Science


Abstract

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,ß-unsaturated enals using only two and three column chromatographic purification steps, respectively. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.


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