An efficient synthesis of (4S,5S,6S)-6-benzyl-4,5-epoxy-6-hydroxy-2-cyclohexen-1-one (2) representing a model compound for the cyclohexenone moiety of scyphostatin (1) was accomplished; the method features masking of the enone system in 10 in the form of the bromo ether 13 (10->11->12->13), aldol coupling of 13 with benzaldehyde to construct the requisite asymmetric quaternary carbon center at the C-6 position (13->14), and epoxide ring formation (21->2) as the key steps. The key intermediate 10 was prepared from commercially available (-)-quinic acid (3).