title: Pyrrolidinones derived from (S)-pyroglutamic acid: penmacric acid and analogues.
abstract: Alkylation reactions using alpha-halolactams or lactam enolates derived from bicyclic lactam templates can proceed with high endo- or exo- diastereoselectivity respectively. In the latter case, stereochemical correction by means of enolate generation and hindered phenol quench is possible with moderate efficiency. This protocol has been applied to the synthesis of protected penmacric acid and its analogues.
authors.affiliation: Department of Chemistry, Dyson Perrins Laboratory, The University of Oxford, South Parks Road, Oxford, OX1 3QY.
authors.forename: Muhammed
authors.initials: M
authors.lastname: Anwar
authors.forename: Jonathan H
authors.initials: JH
authors.lastname: Bailey
authors.forename: Laura C
authors.initials: LC
authors.lastname: Dickinson
authors.forename: Hermia J
authors.initials: HJ
authors.lastname: Edwards
authors.forename: Rajesh
authors.initials: R
authors.lastname: Goswami
authors.forename: Mark G
authors.initials: MG
authors.lastname: Moloney
mesh_terms: D000478:Alkylation; D000596:Amino Acids / Q000138:chemical synthesis*; D002625:Chemistry, Organic / Q000379:methods; D005998:Glycine / Q000031:analogs & derivatives / Q000737:chemistry; D007097:Imines / Q000737:chemistry; D008956:Models, Chemical; D015394:Molecular Structure; D011760:Pyrrolidinones / Q000138:chemical synthesis*; D011761:Pyrrolidonecarboxylic Acid / Q000031:analogs & derivatives / Q000138:chemical synthesis*; D015203:Reproducibility of Results; D013237:Stereoisomerism
chemical_list: D000596:Amino Acids; D007097:Imines; D011760:Pyrrolidinones; C480950:penmacric acid; D011761:Pyrrolidonecarboxylic Acid; D005998:Glycine