The intramolecular Diels–Alder reaction of the ester (3), which is readily obtainable from ‘diacetone glucose,’ gives compound (4) but under the reaction conditions sunstantial 1,3-prototropic shift occurs with the formation of (8).
B. Fraser-Reid, Z. Benkö, R. Guiliano, K. M. Sun and N. Taylor, J. Chem. Soc., Chem. Commun., 1984, 1029 DOI: 10.1039/C39840001029
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