Synthesis and Evaluation as Glycosidase Inhibitors of Isoquinuclidines Mimicking a Distorted β??Mannopyranoside

…, E Lorthiois, M Meyyappan, A Vasella

Index: Boehm, Matthias; Lorthiois, Edwige; Meyyappan, Muthuppalaniappan; Vasella, Andrea Helvetica Chimica Acta, 2003 , vol. 86, # 11 p. 3787 - 3817

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Citation Number: 21

Abstract

Abstract Racemic and enantiomerically pure manno-configured isoquinuclidines were synthesized and tested as glycosidase inhibitors. The racemic key isoquinuclidine intermediate was prepared in high yield by a cycloaddition (tandem Michael addition/aldolisation) of the 3-hydroxy-1-tosyl-pyridone 10 to methyl acrylate, and transformed to the racemic N-benzyl manno-isoquinuclidine 2 and the N-unsubstituted ...