title: Improved synthesis of the epoxy isoprostane phospholipid PEIPC and its reactivity with amines.
abstract: An improved synthesis of the naturally occurring hydroxy ketone 1-palmitoyl-2-(5,6)-epoxyisoprostane E 2- sn-glycero-3-phosphocholine (PEIPC) 1, a compound that plays a role in endothelial activation in atherosclerosis, has been carried out using a PMB ether as the key protecting group. Opening of an intermediate with pentylamine shows that the allylic epoxide is the position of attack by nucleophiles.
authors.affiliation: Departments of Chemistry and Biochemistry, Medicine/Cardiology, and Pathology, University of California, Los Angeles, California 90095, USA. jung@chem.ucla.edu
authors.forename: Michael E
authors.initials: ME
authors.lastname: Jung
authors.forename: Judith A
authors.initials: JA
authors.lastname: Berliner
authors.forename: Lukasz
authors.initials: L
authors.lastname: Koroniak
authors.forename: B Gabriel
authors.initials: BG
authors.lastname: Gugiu
authors.forename: Andrew D
authors.initials: AD
authors.lastname: Watson