Total synthesis of the epoxy isoprostane phospholipids PEIPC and PECPC
ME Jung, JA Berliner, D Angst, D Yue, L Koroniak… - Organic …, 2005 - ACS Publications
ME Jung, JA Berliner, D Angst, D Yue, L Koroniak, AD Watson, R Li
Organic letters, 2005•ACS PublicationsA 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.
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.
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.
ACS Publications