A new overcrowded lactone (3) carrying the 2,8-dioxabicyclo[3.3.0]octane ring system was prepared by a simple treatment of tetraol (1) (prepared from 2,7-dihydroxynaphthalene and glyoxal) with 3,5-xylenol, and readily resolved into its enantiomers having a specific rotation of >800Θ (absolute value). A preliminary experiment demonstrated that 3 would be a promising resolving agent.
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