title: Enantioselective total synthesis of lycopodine.
abstract: 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.
authors.affiliation: Department of Chemistry, Oregon State University, 153 Gilbert Hall, Corvallis, Oregon 97331, USA.
authors.forename: Hua
authors.initials: H
authors.lastname: Yang
authors.forename: Rich G
authors.initials: RG
authors.lastname: Carter
authors.forename: Lev N
authors.initials: LN
authors.lastname: Zakharov
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis*; D003500:Cyclization; D007659:Ketones / Q000138:chemical synthesis; D011807:Quinolizines / Q000138:chemical synthesis*; D013237:Stereoisomerism; D013450:Sulfones / Q000138:chemical synthesis
chemical_list: D000470:Alkaloids; D007659:Ketones; D011807:Quinolizines; D013450:Sulfones; C016542:lycopodine