Total syntheses of bioactive oxidized ethanolamine phospholipids.

[reaction: see text] Truncated ethanolamine phospholipids containing aldehyde functionality, e.g. OVPE, and the corresponding acids, are generated by oxidative cleavage of polyunsaturated phospholipids. To confirm their identities and facilitate studies of the chemistry and biological actions of these analogues of biologically active phosphatidylcholines, e.g. OVPC, total syntheses were developed. An efficient general strategy was used that features selective N-protection of 2-lysophosphatidylethanolamine, and generation of the target compounds by mild deprotection of stable precursors.