title: Alkylation of 2-substituted (6-methyl-2-pyridyl)methyllithium species with epoxides.
abstract: Substituted (6-methyl-2-pyridyl)methyllithium species were reacted with 1,2-epoxyoctane and 2-methyl-2,3-epoxynonane. The monosubstituted epoxide reacted efficiently with lutidyllithium and a number of 2-substituted (6-methyl-2-pyridyl)methyllithium derivatives. The trisubstituted epoxide gave low yields of adducts with all (2-pyridyl)methyllithium species studied. These results are discussed in the context of a proposed synthesis of cananodine.
authors.affiliation: Department of Chemistry, Western Washington University, 516 High Street, Bellingham, Washington 98225-9150, USA. vyvyan@chem.wwu.edu
authors.forename: James R
authors.initials: JR
authors.lastname: Vyvyan
authors.forename: Rebecca C
authors.initials: RC
authors.lastname: Brown
authors.forename: Brian P
authors.initials: BP
authors.lastname: Woods
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis; D000478:Alkylation; D003500:Cyclization; D004852:Epoxy Compounds / Q000737:chemistry*; D008094:Lithium / Q000737:chemistry; D009942:Organometallic Compounds / Q000737:chemistry*; D011725:Pyridines / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000470:Alkaloids; D004852:Epoxy Compounds; D009942:Organometallic Compounds; D011725:Pyridines; C520093:methyllithium; D008094:Lithium