• Chemistry, Medicine
  • Published in
    Organic & biomolecular…
    2009
  • DOI:10.1039/b915796d

Total synthesis of (5R,6R,8R,9S)-(-)-5,9Z-indolizidine 221T using sulfinimine-derived N-sulfinyl beta-amino ketones.

@article{Davis2009TotalSO,
  title={Total synthesis of (5R,6R,8R,9S)-(-)-5,9Z-indolizidine 221T using sulfinimine-derived N-sulfinyl beta-amino ketones.},
  author={Franklin Arnold Davis and Minsoo Song and Hui Qiu and Jing Chai},
  journal={Organic & biomolecular chemistry},
  year={2009},
  volume={7 24},
  pages={
          5067-73
        }
}
The first total asymmetric synthesis of the poison frog alkaloid (-)-221T, a 5,6,8-trisubstituted indolizidine is described. The key core piperidine ring was constructed via an acid catalyzed intramolecular cascade Mannich cyclization reaction of a N-sulfinyl syn-alpha-methyl beta-amino ketone and crotonaldehyde. The beta-amino ketone was prepared via the reaction of prochiral lithium Weinreb amide enolate with an enantiopure N-2,4,6-triisopropylphenylsulfinyl imine.