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: Michael E Jung, Judith A Berliner, Daniela Angst, Dawei Yue, Lukasz Koroniak, Andrew D Watson, Rongsong Li
• Journal: Organic letters (Org Lett) Vol. 7 Issue 18 Pg. 3933-5 (Sep 01 2005) ISSN: 1523-7060 [Print] United States
• PMID: 16119935 (Publication Type: Journal Article, Research Support, N.I.H., Extramural, Research Support, Non-U.S. Gov't, Research Support, U.S. Gov't, P.H.S.)

Chemical References

• 1-palmitoyl-2-(epoxycyclopentenone)-sn-glycero-3-phosphocholine
• 1-palmitoyl-2-(epoxyisoprostane-E2)-sn-glycero-3-phosphocholine
• Epoxy Compounds
• Isoprostanes
• Phosphatidylcholines

Topics

• Epoxy Compounds (chemical synthesis)
• Isoprostanes (chemical synthesis)
• Molecular Structure
• Phosphatidylcholines (chemical synthesis)