Work

Regioselective Synthesis of α-Methyl 2-Methyleneglutarate via a Novel Lactonization−Elimination Rearrangement

Year: 2005

Type: article

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.

Source: The Journal of Organic Chemistry

DOI: 10.1021/jo051854a

Authors: David M. Bartley, James K. Coward

Institution: University of Michigan

Language: English

Topic: Organic Chemistry Synthesis Methods

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: National Cancer Institute, National Institute of General Medical Sciences

Awards: Interdepartmental Training in Pharmacological Sciences, Rational Drug Design Based on Chemical Mechanisms, G510182068, G973650842