Synthesis of C11 chain-extended analogues of N-acetylneuraminic acid

Abstract

The synthesis of novel C₁₁ chain-extended analogues of N-acetylneuraminic acid has been achieved from the N-acetyl-9-hydroxyneuraminic acid derivative 7 via a Swern oxidation/Wittig olefination sequence. In this way the novel α,β-unsaturated ester 12, the saturated ester 13 and the α,β-unsaturated aldehyde 14 of N-acetylneuraminic acid have been prepared in good overall yield.