Stereoselective total syntheses of the naturally occurring enantiomers of N-acetylneuraminic acid and 3-deoxy-D-manno-2-octulosonic acid. A new and stereospecific approach to sialo and 3-deoxy-D-manno-2-octulosonic acid conjugates

Article abstract of DOI:10.1021/ja00220a035

The total syntheses of the title compounds have been achieved. A critical element of these syntheses was the concept of using a furan ring as a surrogate for a carboxylic acid. The furyl diene 22 reacted with the R and S enantiomers of 2-(phenylseleno)pro