Clickable 9-azido-(9-deoxy)- Cinchona alkaloids: synthesis and conformation

The synthesis and conformational preferences of 9-azido-(9-deoxy)- Cinchona alkaloids constituting a novel class of Cinchona alkaloid derivatives of both natural and 9- epi configurations are described. One and two-step preparative syntheses of 9-azido-(9-deoxy)- Cinchona alkaloids have been develop...

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Bibliographic Details
Published in:Tetrahedron: asymmetry 2010-11, Vol.21 (21), p.2740-2745
Main Authors: Kacprzak, Karol, Gierczyk, Błażej
Format: Article
Language:English
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Summary:The synthesis and conformational preferences of 9-azido-(9-deoxy)- Cinchona alkaloids constituting a novel class of Cinchona alkaloid derivatives of both natural and 9- epi configurations are described. One and two-step preparative syntheses of 9-azido-(9-deoxy)- Cinchona alkaloids have been developed, allowing for their easy access on a multigram scale. The stereochemical integrity of these azides has been confirmed from their circular dichroism and specific rotation data. The conformations of the 9-azido Cinchona alkaloids, deduced from both 1H NMR and DFT calculations, show that this class of Cinchona derivatives largely reflect the conformational preferences of the corresponding Cinchona bases; this strategy, therefore, offers a defined chiral and clickable scaffold.
ISSN:0957-4166
1362-511X
DOI:10.1016/j.tetasy.2010.10.023