A3-Coupling Reaction as a Strategy Towards the Synthesis of Alkaloids

A number of aldehydes, alkynols and benzylamines were submitted to A3-coupling reaction, under CuCl catalysis, giving strategically functionalized hydroxy-propargylamines. The procedure allows the use of alkyl as well as aryl aldehydes. Representative substrates were converted into fiveand six-membe...

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Bibliographic Details
Published in:Journal of the Brazilian Chemical Society 2015-01, Vol.26 (1), p.117-123
Main Authors: Carmona, Rafaela C., Wendler, Edison P., Sakae, George H., Comasseto, João V., Santos, Alcindo A. Dos
Format: Article
Language:eng ; por
Subjects:
CHEMISTRY, MULTIDISCIPLINARY
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Summary:A number of aldehydes, alkynols and benzylamines were submitted to A3-coupling reaction, under CuCl catalysis, giving strategically functionalized hydroxy-propargylamines. The procedure allows the use of alkyl as well as aryl aldehydes. Representative substrates were converted into fiveand six-membered cyclic alkaloids by sequential one-pot N-debenzylation/triple bond reduction promoted by Pd, followed by a Mitsunobu-type cyclization.
ISSN:1678-4790
DOI:10.5935/0103-5053.20140223