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Keywords:

  • alkaloids;
  • dihydropyridones;
  • natural products;
  • total synthesis;
  • Tsuji–Trost reaction
Thumbnail image of graphical abstract

Highly stereocontrolled: The total synthesis of frog alkaloid (−)-205B features a chiral N-acylpyridinium salt reaction and an unprecedented trifluoroacetic anhydride mediated addition of an allylstannane to a vinylogous amide. The core was assembled using a Tsuji–Trost allylic amination reaction and a ring-closing metathesis. TIPS=triisopropylsilyl.