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. (C) 2000 Elsevier Science Ltd. All rights reserved.