C3-thia and C3-carba isosteres of a carbocyclic influenza neuraminidase inhibitor, (3R,4R,5S).4-acetamido-5-amino-3-propoxy-1-cyclohexene-1-carboxylic acid

Article abstract of DOI:10.1016/S0960-894X(97)00332-6

The importance of the oxygen atom in the C₃ ether side chain of a carbocyclic influenza neuraminidase inhibitor 3 was investigated by replacement of the C₃ ether oxygen atom of 3 with either a sulfur atom (compound 4) or a carbon atom (compound 5). The regio- and stereospecific syntheses of both isoteres are described starting from (-)-quinic acid.