Chemoenzymatic synthesis of the four diastereoisomers of 4-hydroxypipecolic acid from N-acetyl-(R, S)-allylglycine: chiral scaffolds for drug discovery

…, SJC Taylor, DA Chaplin, R McCague

Index: Lloyd, Richard C.; Smith, Mark E. B.; Brick, Dean; Taylor, Stephen J. C.; Chaplin, David A.; McCague, Raymond Organic Process Research and Development, 2002 , vol. 6, # 6 p. 762 - 766

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Citation Number: 12

Abstract

All four diastereoisomers of 4-hydroxypipecolic acid were prepared in a form conveniently protected for drug discovery applications with the use of industrially scaleable methodology. Resolution of the racemic starting material using proprietary acylases followed by an acyliminium ion cyclisation gave diastereomeric mixtures of 4-formyloxypipecolic acid, which were differentiated using an enzyme-catalysed hydrolysis. The products were separated ...