On the formation of reductic acid from pentoses or hexuronic acids

Article abstract of DOI:10.1016/0008-6215(93)84254-4

Careful hydrolysis of (±)-cis- or (±)-trans-tetrahydro-2,5-dimethoxy-2-furaldehyde dimethyl acetal proceeded via 5,5-dimethoxy-4-oxopentanal to give (±)-trans-4-hydroxy-5-methoxy-2-cyclopenenone and (±)-trans-4,5-dihydroxy-2-cylopentenone. The latter product did not isomerize to 2,3-dihydroxy-2-cyclopentenone (reductic acid) on prolonged reaction. Careful hydrolysis of (±)-cis- or (±)-trans-tetrahydro-2, 5-dimethoxy-2-furaldehyde dimethyl acetal proceeded via 5, 5-dimethoxy-4-oxopentanal to give (±)-tran-4-hydroxy-5-methoxy-2-cyclopentenone and (±)-trans-4 ,5-dihydroxy-2-cyclopentenone. The latter product did not isomerize to 2,3-dihydroxy-2-cyclopentenone (reductic acid) on prolonged reaction.