An Efficient Synthesis of (S)-5-Hydroxymethyl-2(5H)-furanone.

Abstract A three step synthesis of the title compound 1a from D-ribono-1,4-lactone in 48% yield is described. The concept centers on a novel NaHSO3-induced trans -Br-OAc elimination of the readily prepared bromo-acetate mixture 3a,b to the corresponding butenolides 1e and 1f , the former of which, on hydrolysis and purification, yields pure 1a .