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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.

SUBMITTER: Vyvyan JR

PROVIDER: S-EPMC2635110 | biostudies-literature | 2009 Feb

REPOSITORIES: biostudies-literature

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Alkylation of 2-substituted (6-methyl-2-pyridyl)methyllithium species with epoxides.

Vyvyan James R JR Brown Rebecca C RC Woods Brian P BP

The Journal of organic chemistry 20090201 3

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. ...[more]

PMID: 19113936

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