Total synthesis of the N,C-coupled naphthylisoquinoline alkaloids ancistrocladinium A and B and related analogues.

@article{Bringmann2010TotalSO,
  title={Total synthesis of the N,C-coupled naphthylisoquinoline alkaloids ancistrocladinium A and B and related analogues.},
  author={G. Bringmann and Tanja Gulder and Barbara Hertlein and Y. Hemberger and F. Meyer},
  journal={Journal of the American Chemical Society},
  year={2010},
  volume={132 3},
  pages={
          1151-8
        }
}
The N,C-coupled naphthyldihydroisoquinoline alkaloids ancistrocladinium A (3) and B (4), which possess an unprecedented iminium-aryl axis and show high in vitro antileishmanial activities, have been synthesized via a short sequence of eight linear steps, without the need of protecting groups. Key steps were a Buchwald-Hartwig amination and a Bischler-Napieralski cyclization, preferentially leading to the naturally predominant M-atropo-diastereomer in the case of 3, while the N,C-axis is… Expand
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