Water → HCID 23614998, compound

Participants

Reaction Steps

To a solution of phenol viii (200 mg, 0.65 mmol) in DMF (10 mL) was added cesium carbonate (419 mg, 1.29 mmol) and methyl iodide (88 μL, 1.42 mmol). The mixture was stirred at room temperature for 1 h and then poured into cold water (50 mL). The mixture was then extracted with EtOAc (5×50 mL). The combined extracts were washed with brine and dried (MgSO4). The solvent was removed under reduced pressure to provide the crude tetracyclic lactone ether ix (163 mg) as a yellow solid that was used in the next step without further purification. A small portion of the crude ix was purified by reverse phase preparative HPLC for characterization. 1H NMR (acetone-d6) δ 10.90 (br s, 1H), 8.59 (d, J=8.4, 1H), 7.34 (t, J=8.4 Hz, 1H), 7.21 (d, J=8.4, 1H), 6.98 (d, J=8.4, 1H), 6.90 (d, J=8.4 Hz, 1H), 5.93 (br s, 1H), 4.01 (s, 3H), 1.34 (s, 6H). Anal. Calcd for C18H16N2O4: C, 66.66; H, 4.97; N, 8.64. Found: C, 66.66; H, 4.79; N, 8.96.

Provenance & Evidence