Diethyl 9-(1,3-benzodioxol-5-yl)-6-hydroxy-benzo[g][1,3]benzodioxole-7,8-dicarboxylate → 10-Benzo[1,3]dioxol-5-yl-6-hydroxy-7H-furo[3',4':6,7]naphtho[1,2-d][1,3]dioxol-9-one

Participants

Reaction Steps

A solution of 33 (45.2 mg, 0.1 mmol) in THF (1 mL) was added dropwise to a suspension of lithium aluminum hydride (7.6 mg, 0.2 mmol) in THF (1 mL) at 0° C. The mixture was stirred at room temperature for 2 h and quenched with aqueous saturated Na2SO4 solution, and then extracted with CHCl3 (2×30 mL). After evaporation of organic solvent, the residue was purified by column chromatography on silica gel using CH2Cl2/MeOH (20:1, v/v) to give 34 (36 mg, 99%) as a yellow powder. mp 257° C. (decomp.); 1H NMR (DMSO-d6) δ 10.67 (s, 1H, 4OH), 7.94 (d, 1H, H5, J=9.0 Hz), 7.44 (d, 1H, H6, J=9.0 Hz), 6.84 (d, 1H, H5′, J=8.1 Hz), 6.79 (d, 1H, H2′, J=1.5 Hz), 6.66 (dd, 1H, H6′, J=1.5, 8.1 Hz), 6.04 (AB, 2H, 3′,4′-OCH2O—, Δδ=6.0 Hz, J=0.6 Hz), 5.88 (AB, 2H, 7,8-OCH2O—, Δδ=6.3 Hz, J=0.9 Hz), 5.32 (s, 2H, lactone-CH2—); MS (FAB, positive) m/z 365 [M+H]+.

Provenance & Evidence