Total synthesis of (+)-hyacinthacine A2 based on SmI2-induced nitrone umpolung.

@article{Desvergnes2005TotalSO,
  title={Total synthesis of (+)-hyacinthacine A2 based on SmI2-induced nitrone umpolung.},
  author={St{\'e}phanie Desvergnes and Sandrine Py and Yannick Vall{\'e}e},
  journal={The Journal of organic chemistry},
  year={2005},
  volume={70 4},
  pages={1459-62}
}
[reaction: see text] A concise total synthesis of (+)-hyacinthacine A(2), a polyhydroxylated pyrrolizidine alkaloid, is described using our recently discovered inversion of the C-N bond polarity in nitrones. In the key step, the diastereoselective reductive coupling of a L-xylose-derived cyclic nitrone with ethyl acrylate allowed the assembly of the bicyclic core of the target molecule, by way of a tandem formation of the C-C and C-N bonds. The method opens a novel, short, and general route for… CONTINUE READING