Photochemical ring contraction in the presence of sodium cyanobrohydride of 5-hydroxy-2-[(E)-prepenyl]-4-pyrone (11a), which was readily synthesised from kojic acid, gave (±)-terrein {trans-4,5-dihydroxy-3-[(E)-propenyl]cyclopent-2-enone}(1) as well as the (±)-isomer (12) with the hydroxy-groups cis.
D. H. R. Barton and L. A. Hulshof, J. Chem. Soc., Perkin Trans. 1, 1977, 1103 DOI: 10.1039/P19770001103
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