Syntheses of arsinolipids: Non-isosteric analogues of phospholipids

Reaction of alkaline benzenearsonous and 2,3-dihydroxypropylarsonous acids with rac-glycidol affords the corresponding arsinic acids, which after redu ction with thiophenol are acylated with either fatty-acid chlorides/pyridin e or fatty acids/dicyclohexexylcarbodiimide/4-dimethylaminopyridine and oxi dized with hydrogen peroxide to give the arsinolipids (rac-2,3-diacyloxypro pyl)phenylarsinic and bis-(rac-2,3-diacyloxypropyl)arsinic acids. The latte r is a non-isosteric analogue of bisphosphatidic acid. Copyright (C) 2000 J ohn Wiley & Sons, Ltd.