Synthesis of carbocyclic analogues of 3-deoxy-d-manno-2-octulosonic acid and N-acetylneuraminic acid

A carbocyclic analogue of N-acetylneuraminic acid was synthesised from the Diels-Alder endo-adduct of furan and acrylic acid, and its ammonium salt was subjected to bioassay. In addition, carbocyclic analogues of 3-deoxy-d-manno-2-octulosonic acid were synthesised in racemic form from the same synthetic intermediate.