A3-Coupling Reaction as a Strategy Towards the Synthesis of Alkaloids
JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY(2015)
Abstract
A number of aldehydes, alkynols and benzylamines were submitted to A(3)-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 five- and six-membered cyclic alkaloids by sequential one-pot N-debenzylation/triple bond reduction promoted by Pd, followed by a Mitsunobu-type cyclization.
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Key words
hydroxy-propargylamines,A(3)-coupling,C-H activation,cyclic alkaloids
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