[C:1]([O:5]O)([CH3:4])([CH3:3])[CH3:2].[OH:7][CH2:8][CH:9]1CCC=CO1.C(OCC)(=[O:17])C>C1(C)C=CC=CC=1.[O-][V]([O-])([O-])=O.[Na+].[Na+].[Na+]>[C:1]12([CH2:4][OH:17])[O:5][CH:3]1[CH2:9][CH2:8][O:7][CH2:2]2Tert-butyl hydroperoxide (5.5M, 4.73 mmoles) was added to a mixture of vanadyl acetoacetonate (0.058 g, 0.22 mmoles) and hydroxymethyldihydro-pyran (0.5 g, 4.38 mmoles) in 16.2 ml of toluene at 85° C. After stirring for 5 minutes, TLC showed the reaction to be complete. The mixture was diluted with ethyl acetate and washed with 1 M hydrochloric acid followed by a wash with a saturated sodium bicarbonate solution. The ethyl acetate layer was dried over sodium sulfate, filtered and concentrated in vacuo to yield a light yellow oil (0.4 g, 70%). 1H NMR (D6 acetone, 400 MHz) δ 3.21 (bs, 1H), 3.36-3.42 (m, 2H), 3.48 (dd, J=6.64 Hz and 12.04 Hz, 1H), 3.6 (dd, J=5.61 Hz and 12.04 Hz, 1H), 3.74 (d, J=13.07 Hz, 1H), 3.87 (dd, J=5.6 Hz and 6.64 Hz, 1H), 4.02 (d, J=13.07 Hz, 1H).
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