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Catalytic Asymmetric Total Synthesis of (-)-Garryine via an Enantioselective Heck Reaction.

Chuang LiFei LuYukun CaiCheng ZhangYu ShaoYuanyuan ZhangXiao-Yu LiuYong Qin
Published in: Journal of the American Chemical Society (2023)
The first asymmetric total synthesis of the hexacyclic veatchine-type C 20 -diterpenoid alkaloid (-)-garryine is presented. Key steps include a Pd-catalyzed enantioselective Heck reaction, a radical cyclization, and a photoinduced C-H activation/oxazolidine formation sequence. Of note, a highly enantioselective Heck reaction developed in this work provides efficient access to 6/6/6 tricyclic compounds, in particular, containing a C19-functionalitiy, which is useful for diverse transformations.
Keyphrases
  • electron transfer
  • amino acid
  • crystal structure
  • ionic liquid