Synthesis of (2R)-2-bromodehydroquinic acid and (2R)-2-fluorodehydroquinic acid

Abstract

(2R)-2-Bromodehydroquinic acid and (2R)-2-fluorodehydroquinic acid† have each been synthesised in six steps from quinic acid via the common intermediate 6. The syntheses exploit the selective protection of the 4-hydroxy group of the quinic acid lactone 3 with tert-butyldimethylsilyl chloride.