EFFICIENT ASYMMETRIC-SYNTHESIS OF (R)-3-HYDROXYTETRADECANOIC AND ALKANOYLOXYTETRADECANOIC ACIDS AND METHOD FOR THE DETERMINATION OF ENANTIOMERIC PURITY

An efficient synthesis of the (R)-3-hydroxy- and alkanoyloxytetradecan oic acid components of bacterial lipid A has been achieved using a Ru( II)-Binap-catalyzed low-pressure hydrogenation in the key step. The en antiomeric purity of p-bromophenacyl eater intermediate 4 could be ass essed directly by chiral HPLC-obviating separate derivatization steps and/or chiral NMR shift studies. Copyright (C) 1996 Elsevier Science L td.