A total synthesis of racemic and optically active terrein (trans-4,5-dihydroxy-3-[(E)-1-propenyl]-2-cyclopenten-1-one)

Article abstract of DOI:10.1016/S0957-4166(00)86329-6

Two routes to terrein (1), employing a novel ring contraction of 6-alkoxy-2,3-dihydro-6H-pyran-3-ones (5, 13) are described. Separation into enantiomers was carried out by classical resolution via diastereomeric camphanic acid ester intermediates (14, 15)