AN EFFICIENT SYNTHESIS OF (S)-5-HYDROXYMETHYL-2(5H)-FURANONE

Article abstract of DOI:10.1016/S0040-4039(00)96107-0

A three step synthesis of the title compound 1a from D-ribono-1,4-lactone in 48percent 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.