Total synthesis of the epoxy isoprostane phospholipids PEIPC and PECPC.
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]
Jung
Michael E
ME
Departments of Chemistry and Biochemistry, University of California-Los Angeles, Los Angeles, CA 90095, USA. jung@chem.ucla.edu
Berliner
Judith A
JA
Angst
Daniela
D
Yue
Dawei
D
Koroniak
Lukasz
L
Watson
Andrew D
AD
Li
Rongsong
R
D004852:Epoxy Compounds / Q000138:chemical synthesis*; D028421:Isoprostanes / Q000138:chemical synthesis*; D015394:Molecular Structure; D010713:Phosphatidylcholines / Q000138:chemical synthesis*
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