Asymmetric total synthesis of (-)-stenine and 9a-epi-stenine.

@article{Fujioka2012AsymmetricTS,
  title={Asymmetric total synthesis of (-)-stenine and 9a-epi-stenine.},
  author={H. Fujioka and Kenji Nakahara and Naoyuki Kotoku and Yusuke Ohba and Yasushi Nagatomi and Tsung-Lung Wang and Y. Sawama and Kenichi Murai and Kie Hirano and Tomohiro Oki and Shintaro Wakamatsu and Y. Kita},
  journal={Chemistry},
  year={2012},
  volume={18 43},
  pages={
          13861-70
        }
}
A route for the asymmetric synthesis of (-)-stenine, a member of the Stemona alkaloid family used as folk medicine in Asian countries, is described. The key features of the sequence employed include stereoselective transformations on a cyclohexane ring controlled by a chiral auxiliary unit and an intramolecular Mitsunobu reaction to construct the perhydroindole ring system. By using an intermediate in the route to (-)-stenine, an asymmetric synthesis of 9a-epi-stenine was also executed. The C… Expand
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