Improved synthesis of the epoxy isoprostane phospholipid PEIPC and its reactivity with amines.
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.
Jung
Michael E
ME
Departments of Chemistry and Biochemistry, Medicine/Cardiology, and Pathology, University of California, Los Angeles, California 90095, USA. jung@chem.ucla.edu
Berliner
Judith A
JA
Koroniak
Lukasz
L
Gugiu
B Gabriel
BG
Watson
Andrew D
AD