Regioselective synthesis of alpha-methyl 2-methyleneglutarate via a novel lactonization-elimination rearrangement.
[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.
Bartley
David M
DM
Department of Medicinal Chemistry, University of Michigan, Ann Arbor, Michigan 48109-1055, USA.
Coward
James K
JK
D005977:Glutarates / Q000138:chemical synthesis* / Q000737:chemistry; D007783:Lactones / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
D005977:Glutarates; D007783:Lactones; C511848:alpha-methyl 2-methyleneglutarate