The total synthesis of ()-xyloketal D and its enantiomer have been achieved by the reaction of an ortho-quinone methide with (4 R)-and (4 S)-4, 5-dihydro-2, 4-dimethylfuran via a diastereoselective inverse electron demand Diels Alder reaction. This total synthesis confirmed the absolute stereochemistry of the natural product. The ortho-quinone methide was generated by reaction of an appropriately functionalized Mannich base with methyl ...