A short, chiral synthesis of unnatural, cytotoxic ether-linked phospholipids is reported in which the key step is the very high regio-and stereospecific nucleophilic opening of the p- toluenesulfonate (la, lb) or tert-butyldiphenylsilyl ether (6a, 6b) derivatives of (R)-or (S)- glycidol with 1-hexadecanol using boron trifluoride etherate as catalyst. The enantiomeric excess of the ring-opened products was> 94%, as judged by'H NMR and chiral HPLC ...
