Total Synthesis of Aaptamine, Demethyloxyaaptamine, and Their 3-Alkylamino Derivatives
2019
Gao, Yuan | Yang, Fan | Sun, Fan | Liu, Lei | Liu, Bo | Wang, Shu-Ping | Cheng, Chun-Wei | Liao, Hongze | Lin, Hou-Wen
A simple and efficient synthetic route for preparing the benzonaphthyridine framework is reported. Only seven steps are needed for the assembly of 3-alkylamino aaptamine from inexpensive isoquinoline 6 by this route with about 20% overall yield. The two key steps are a novel palladium-catalyzed reductive cyclization with Mo(CO)₆ as reductant to form aaptamine and demethyloxyaaptamine and a hydrogen-bond-mediated oxidative alkylamination to account for the complete regioselectivity.
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