Bicyclic peptidomimetic tetrahydrofuro [3, 2-b] pyrrol-3-one and hexahydrofuro [3, 2-b] pyridine-3-one based scaffolds: synthesis and cysteinyl proteinase inhibition

M Quibell, A Benn, N Flinn, T Monk, M Ramjee…

Index: Quibell, Martin; Benn, Alex; Flinn, Nick; Monk, Tracy; Ramjee, Manoj; Wang, Yikang; Watts, John Bioorganic and Medicinal Chemistry, 2004 , vol. 12, # 21 p. 5689 - 5710

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Citation Number: 44

Abstract

A stereoselective synthesis of (3aS, 6aR)-tetrahydrofuro [3, 2-b] pyrrol-3-ones and (3aS, 7aR)-hexahydrofuro [3, 2-b] pyridine-3-ones has been developed through Fmoc protected scaffolds 12 and 13. A key design element within these novel bicyclic scaffolds, in particular the 5, 5-fused system, was the inherent stability of the cis-fused geometry in comparison to that of the corresponding trans-fused. Since the bridgehead stereocentre situated β to the ...