Efficient asymmetric synthesis of (R)-3-hydroxy- and alkanoyloxytetradecanoic acids and method for the determination of enantiomeric purity

Article abstract of DOI:10.1016/S0957-4166(96)00464-8

An efficient synthesis of the (R)-3-hydroxy- and alkanoyloxytetradecanoic acid components of bacterial lipid A has been achieved using a Ru(II)-Binap-catalyzed low-pressure hydrogenation in the key step. The enantiomeric purity of p-bromophenacyl ester intermediate 4 could be assessed directly by chiral HPLC - obviating separate derivatization steps and/or chiral NMR shift studies.