title: Pyridone annulation via tandem Curtius rearrangement/6π-electrocyclization: total synthesis of (-)-lyconadin C.
abstract: A concise, enantioselective total synthesis of the Lycopodium alkaloid (-)-lyconadin C was achieved in 12 steps and high overall yield. Key features include construction of a luciduline congener through Mannich-type cyclization and a one-pot, tandem Curtius rearrangement/6π-electrocyclization to fashion the 2-pyridone system of lyconadin C.
authors.affiliation: Department of Chemistry, The University of Vermont, 82 University Place, Burlington, Vermont 05405, USA.
authors.forename: Xiayun
authors.initials: X
authors.lastname: Cheng
authors.forename: Stephen P
authors.initials: SP
authors.lastname: Waters
mesh_terms: D000470:Alkaloids / Q000737:chemistry*; D003500:Cyclization; D032502:Lycopodium / Q000737:chemistry*; D015394:Molecular Structure; D011083:Polycyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D011728:Pyridones / Q000737:chemistry*; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D011083:Polycyclic Compounds; D011728:Pyridones; D011804:Quinolines; C582718:lyconadin C; C410447:luciduline
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