Total synthesis of (±)-Gelsemoxonine.

@article{Diethelm2013TotalSO,
  title={Total synthesis of (±)-Gelsemoxonine.},
  author={S. Diethelm and E. Carreira},
  journal={Journal of the American Chemical Society},
  year={2013},
  volume={135 23},
  pages={
          8500-3
        }
}
Gelsemoxonine (1) is a Gelsemium alkaloid incorporating an unusual azetidine. Its total synthesis was achieved employing a novel ring contraction of a spirocyclopropane isoxazolidine to furnish a β-lactam intermediate. This β-lactam ring was further elaborated into the azetidine of Gelsemoxonine. In addition, the synthesis includes a highly diastereoselective reductive Heck cyclization for the installation of the oxindole ring system as well as a directed hydrosilylation of an alkyne to access… Expand
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