Formal Synthesis of (+)- and (-)-Ferruginine

A formal synthesis of the naturally occurring (+)‐ferrugine and of its enantiomer starting from the commercially available tropinone is reported. The desymmetrization of tropinone was achieved through formation of diastereomeric unsaturated sulfoxides using the Andersen procedure. Introduction of th...

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Bibliographic Details
Published in:European Journal of Organic Chemistry 2007-10, Vol.2007 (28), p.4752-4757
Main Authors: Piccardi, Riccardo, Renaud, Philippe
Format: Article
Language:English
Subjects:
Alkaloids
Chemical Sciences
Conjugate addition
Desymmetrization
Organic chemistry
Sulfoxides
Tropanes
α,β‐Unsaturated sulfones
β-Unsaturated sulfones
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Summary:A formal synthesis of the naturally occurring (+)‐ferrugine and of its enantiomer starting from the commercially available tropinone is reported. The desymmetrization of tropinone was achieved through formation of diastereomeric unsaturated sulfoxides using the Andersen procedure. Introduction of the acetyl C(2) side chain was achieved by conjugate addition of lithiated ethyl vinyl ether to an unsaturated sulfone. N‐Boc‐Norferruginine, an advanced intermediate for the synthesis of ferruginine, was prepared in six steps and 19 % overall yield. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.200700427