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Articles • J. Braz. Chem. Soc. 26 (1) • Jan 2015 • https://doi.org/10.5935/0103-5053.20140223   copy

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

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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.

hydroxy-propargylamines; A3-coupling; C–H activation; cyclic alkaloids

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