Efficient syntheses of (−)-shikimate and (−)-quinate 3-phosphate via trans vicinal diol protection with 2,2,3,3-tetramethoxybutane (TMB) of shikimic and quinic acids

(−)-Shikimate 3-phosphate and (−)-quinate 3-phosphate can be synthesized by selective protection of their trans diol functionality using 2,2,3,3-tetramethoxybutane (TMB) using d-(−)-shikimic acid and d-(−)-quinic acid as starting materials. This versatile reagent facilitates the synthesis of these important biological targets in fewer steps than previously reported. By the proper choice of protecting group for C-3 hydroxyl in d-(−)-quinic acid, it can be converted to a key intermediate in the synthesis of (−)-shikimate 3-phosphate.