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

✍ Scribed by David S. Keegan; Steven R. Hagen; David A. Johnson

Publisher
Elsevier Science
Year
1996
Tongue
English
Weight
310 KB
Volume
7
Category
Article
ISSN
0957-4166

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✦ Synopsis

An efficient synthesis of the (R)-3-hydroxy-and alkanoyloxytetradecanoic acid components of bacterial lipid A has been achieved using a Ru(lI)-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.

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