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Keywords:

  • indolizidines;
  • iridium;
  • pyrrolidines;
  • pyrrolizidines;
  • total synthesis

Abstract

A broadly applicable route to trans-2,5-disubstituted pyrrolidines has been developed. Key steps are an asymmetric iridium-catalyzed allylic amination, a Suzuki–Miyaura coupling, and an intramolecular aza-Michael addition. Enantiomeric excesses in the range of 93–99 % ee have been achieved. Total syntheses of the alkaloids (−)-225 C, (+)- and (−)-223 H (xenovenine), (+)-223 AB, (+)-195 B, and (+)-223 R have been carried out as applications.