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Keywords:

  • alkaloids;
  • asymmetric synthesis;
  • cyclization;
  • Michael addition;
  • Sarain A;
  • total synthesis
Thumbnail image of graphical abstract

A powerful chiral building block: A concise enantioselective synthesis of the diazatricyclic core of sarain A has been accomplished. The novel strategy relies upon the versatile chiral building block (R)-1 (see scheme), and features a tandem Horner–Wadsworth–Emmons–aza-Michael reaction, an intramolecular Michael reaction, and the diastereoconvergent formation of the third ring. Diazatricyclic core 2 possesses all of the necessary functionality for further elaboration into sarain A.