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The synthesis of two new Huperzine A analogues is reported. Both products present an amino substituted benzo-fused system in place of the pyridone ring of the natural alkaloid. The synthetic strategy to the two analogues is based on three different key palladium-catalyzed steps, namely a carbonylation reaction, an epoxide isomerization and a bicycloannulation reaction.
The synthesis of ethyl (2-acetyl-1-cyano-1,2,3,4-tetrahydro-1-isoquinolyl)acetate was accomplished by cyanation/acylation of the dihydroquinoline ring system. The selective cobalt boride catalyzed reduction of the cyano group of the cyanoester intermediate was the key step to obtain the corresponding ethyl (1-aminomethyl-2-acetyl-1,2,3,4-tetrahydro-1-isoquinolyl)acetate which was cyclized by exposure...
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