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Keywords:

  • alkaloids;
  • azomethine ylide;
  • cycloaddition;
  • radical reactions;
  • stereoselectivity
Thumbnail image of graphical abstract

To the core: The first total synthesis of (−)-lycoposerramine-S has been accomplished in 14 steps. The synthesis features the facile construction of the tetracyclic core through an intramolecular 1,3-dipolar cycloaddition of an azomethine ylide, with unexpected stereoselectivity, an 5-exo-trig radical cyclization, and an alkylation of p-nosyl (Ns) amide. TBS=tert-butyldimethylsilyl.