Regioselective synthesis of alpha-methyl 2-methyleneglutarate via a novel lactonization-elimination rearrangement.

ABSTRACT: [reaction: see text] A facile route to the alpha-methyl ester of 2-methyleneglutarate via a three-step sequence from 3-hydroxymethylcyclopentene is described. Regioselective formation of the monoacid from a diester precursor proceeds via a novel fluoride-mediated, tandem deprotection/rearrangement of O-silyl 2-(hydroxymethyl)dimethylglutarate.

SUBMITTER: Bartley DM 

PROVIDER: S-EPMC2082008 | biostudies-literature | 2006 Jan

REPOSITORIES: biostudies-literature