Stereoselective synthesis and sialidase inhibition properties of KDO-based glycosyloxathiins

Abstract

The stereoselective synthesis of KDO-based glyco-1,4-oxathiins is described. Relying on a totally diastereoselective inverse electron demand hetero Diels-Alder, α? α′-dioxothiones as electron-poor heterodienes, and glycals as electron-rich dienophiles, reacted to give, in high yield, the KDO-based glyco derivatives 11 and 12a-c. Taking into account their structural features, biological tests have been run to evaluate the properties of 11 and 12a as sialidase inhibitors. The synthetic and biological data reported confirmed the versatility of this powerful [4+2] cycloaddition and showed the KDO-based cycloadduct 11 as attractive scaffold for the development of new sialidase inhibitors.©ARKAT-USA, Inc.