An efficient route to all eight stereoisomers of a tri-functionalised cyclopentane scaffold for drug discovery

…, SJC Taylor, DA Chaplin, G Casy, R McCague

Index: Smith, Mark E.B.; Lloyd, Michael C.; Derrien, Nadine; Lloyd, Richard C.; Taylor, Stephen J.C.; Chaplin, David A.; Casy, Guy; McCague, Raymond Tetrahedron Asymmetry, 2001 , vol. 12, # 5 p. 703 - 705

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Citation Number: 21

Abstract

3-(tert-Butoxycarbonylamino)-4-hydroxycyclopentanecarboxylic acid methyl esters are conformationally rigid and potentially valuable scaffolds for pharmaceutical discovery. 1 We have recently described an approach to these targets that is primarily concerned with the selectivity of hydrogenation reactions on cyclopent-1-enecarboxylate intermediates. 2 Epoxidations with Oxone® were employed to introduce the oxygen functionality, but we encountered poor volume efficiency and low ...

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