The Journal of Organic Chemistry

Regiospecific opening of glycidyl derivatives mediated by boron trifluoride. Asymmetric synthesis of ether-linked phospholipids

PN Guivisdalsky, R Bittman

Index: Guivisdalsky, Pedro N.; Bittman, Robert Journal of Organic Chemistry, 1989 ,  vol. 54,  # 19  p. 4637 - 4642

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Citation Number: 78

Abstract

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 ...