Chemistry of shikimic acid derivatives. Synthesis of specifically labelled shikimic acid at C-3 or C-4

Abstract

Specifically labeled shikimic acids with tritium or deuterium at positions C-3 or C-4 were synthesized. Commercially available L-shikimic acid was converted to its 3- and 4-ketones, after suitable protection of the hydroxy¡ groups at C-4,C-5 and C-3,C-5. Reduction of the 3-keto- or 4-keto-shikimic acid derivatives with sodium borodeuteride and deprotection gave mostly 3-D-epi-shikimic acid or 4-D-shikimic acid. An internally assisted inversion of the 3-D-epi-shikimic acid derivative and deprotection gave 3-D-shikimic acid.