5840
T. Yakura et al. / Tetrahedron 66 (2010) 5833e5840
11. (a) Marcotullio, M. C.; Epifano, F.; Curini, M. Trends Org. Chem. 2003, 10,
21e34; (b) Gandhari, R.; Maddukuri, P. P.; Vinod, T. K. J. Chem. Educ. 2007, 84,
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2.07e2.22 (1H, m), 2.30 (2H, d, J 6.9 Hz), 5.00 (2H, d, J 1.9 Hz), 6.69
(1H, br q, J 2.0 Hz), 6.77 (1H, d, J 10.0 Hz), 6.80 (1H, dd, J 10.0,
1.0 Hz); dC (75 MHz, CDCl3) 22.5 (2), 25.7, 43.1, 59.2, 131.3, 136.3,
136.4, 143.1, 171.9, 185.9, 186.7; m/z (EI) 222 (Mþ); HRMS, found
222.08822. C12H14O4 requires 222.08921.
Using CAN oxidation: A mixture of 12 (51 mg, 0.2 mg) and CAN
(329 mg, 0.6 mmol) in CH3CNeH2O (2:1, 3 mL) was stirred at room
temperature for 15 min. The reaction mixture was diluted with
ethyl acetate and washed with water. The organic layer was then
washed with aqueous saturated sodium bicarbonate solution and
dried, concentrated. The residue was purified by column chroma-
tography on silica gel (10% ethyl acetate in hexane) to give pure 13
(29 mg, 69%).
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