Synthetic approaches to either homochiral or achiral derivatives of 3-hydroxy-2(5H)-furanone (isotetronic acid)

Article abstract of DOI:10.1016/S0040-4020(01)81841-X

Several title compounds were synthesized according to new methods based either on the use of D-ribonolactone as a chiral precursor or on the cyclization of 2,4-dioxopentanoic acid as a suitable achiral precursor. Base-induced elimination and subsequent acid-promoted ring contraction is an efficient protocol for the preparation of isotetronic acids from 2-O-alkyl-3,4-O-benzylidene-D-ribono-1,5-lactone derivatives.