Sialidase inhibitors related to GG167: Synthesis of analogues via an inverse demand hetero Diels Alder reaction

Article abstract of DOI:10.1016/0040-4039(96)01408-6

An inverse demand hetero Diels Alder strategy has been utilised for the synthesis of novel dihydropyrans as potential inhibitors of influenza virus sialidase. Cyclisation of 1-methoxy-2-acetamido ethene with 2-oxo-4-butoxycarbonylamino but-3-(Z)-enoic acid t-butyl ester in the presence of tin (IV) chloride afforded a mixture of regio- and stereochemical isomers which were further elaborated to analogues of GG167.