title: Total synthesis of the epoxy isoprostane phospholipids PEIPC and PECPC.
abstract: A total synthesis of the naturally occurring hydroxy ketone PEIPC 1, a compound that plays a role in endothelial activation in atherosclerosis, has been completed via a triply convergent preparation of a protected EI derivative 13 from 3,5-diacetoxycyclopentene 7, pentane-1,5-diol, and vinyllithium, using Sharpless epoxidation and enzymatic resolution as key steps. Final coupling with lyso-PC 16 and silyl group deprotection gave PECPC 2 and PEIPC 1, which showed the same activity as natural PECPC and PEIPC. [reaction: see text]
authors.affiliation: Departments of Chemistry and Biochemistry, University of California-Los Angeles, Los Angeles, CA 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: Daniela
authors.initials: D
authors.lastname: Angst
authors.forename: Dawei
authors.initials: D
authors.lastname: Yue
authors.forename: Lukasz
authors.initials: L
authors.lastname: Koroniak
authors.forename: Andrew D
authors.initials: AD
authors.lastname: Watson
authors.forename: Rongsong
authors.initials: R
authors.lastname: Li
mesh_terms: D004852:Epoxy Compounds / Q000138:chemical synthesis*; D028421:Isoprostanes / Q000138:chemical synthesis*; D015394:Molecular Structure; D010713:Phosphatidylcholines / Q000138:chemical synthesis*
chemical_list: C500238:1-palmitoyl-2-(epoxycyclopentenone)-sn-glycero-3-phosphocholine; C500237:1-palmitoyl-2-(epoxyisoprostane-E2)-sn-glycero-3-phosphocholine; D004852:Epoxy Compounds; D028421:Isoprostanes; D010713:Phosphatidylcholines