Conjugate addition of lithiated methyl pyridines to enones.
Preparatively useful conjugate addition of lithiated methyl pyridines to cyclic and acyclic enones is reported. Addition of 2-picoline to 3-penten-2-one led to a concise synthesis of the alkaloids (+/-)-senepodine G and (+/-)-cermizine C.
Taber
Douglass F
DF
Department of Chemistry and Biochemistry, University of Delaware, Newark, Delaware 19716, USA. taberdf@udel.edu
Guo
Pengfei
P
Pirnot
Michael T
MT
D003517:Cyclopentanes / Q000737:chemistry*; D006574:Heterocyclic Compounds, 2-Ring / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010847:Picolines / Q000737:chemistry*; D013237:Stereoisomerism
D003517:Cyclopentanes; D006574:Heterocyclic Compounds, 2-Ring; D010847:Picolines; C518697:cermizine C; C518698:senepodine G; C530793:2-picoline