Enantioselective total synthesis of lycopodine.
The first enantioselective total synthesis of lycopodine has been completed. Key steps include a highly diastereoselective organocatalyzed cyclization of a keto sulfone to establish the key C7 and C8 stereocenters and a tandem 1,3-sulfonyl shift/intramolecular Mannich cyclization to form the tricyclic core.
Yang
Hua
H
Department of Chemistry, Oregon State University, 153 Gilbert Hall, Corvallis, Oregon 97331, USA.
Carter
Rich G
RG
Zakharov
Lev N
LN
D000470:Alkaloids / Q000138:chemical synthesis*; D003500:Cyclization; D007659:Ketones / Q000138:chemical synthesis; D011807:Quinolizines / Q000138:chemical synthesis*; D013237:Stereoisomerism; D013450:Sulfones / Q000138:chemical synthesis
D000470:Alkaloids; D007659:Ketones; D011807:Quinolizines; D013450:Sulfones; C016542:lycopodine