1: 79 percent / glacial HOAc, drierite / ethanol / 4 h / Heating 2: 70.5 percent / diphenyl ether / 0.42 h / 255 °C 3: 93 percent / POCl3 / 2 h / Heating 4: 86 percent / methanol / 5 h / 120 °C 5: 1) THF, hexane, -70 deg C, 2 min, 2) to -40 deg C View Scheme

1: 96 percent / 2,4,4,6-tetrabromo-2,5-cyclohexadienone / CH2Cl2 / -5 deg C to RT 2: 79 percent / glacial HOAc, drierite / ethanol / 4 h / Heating 3: 70.5 percent / diphenyl ether / 0.42 h / 255 °C 4: 93 percent / POCl3 / 2 h / Heating 5: 86 percent / methanol / 5 h / 120 °C 6: 1) THF, hexane, -70 deg C, 2 min, 2) to -40 deg C View Scheme

1: 86 percent / methanol / 5 h / 120 °C 2: 1) THF, hexane, -70 deg C, 2 min, 2) to -40 deg C View Scheme

1: 93 percent / POCl3 / 2 h / Heating 2: 86 percent / methanol / 5 h / 120 °C 3: 1) THF, hexane, -70 deg C, 2 min, 2) to -40 deg C View Scheme

1: 70.5 percent / diphenyl ether / 0.42 h / 255 °C 2: 93 percent / POCl3 / 2 h / Heating 3: 86 percent / methanol / 5 h / 120 °C 4: 1) THF, hexane, -70 deg C, 2 min, 2) to -40 deg C View Scheme

n-butyllithium 1) THF, hexane, -70 deg C, 2 min, 2) to -40 deg C; Yield given. Multistep reaction. Yields of byproduct given;

1) THF, hexane, -70 deg C, 2 min, 2) to -40 deg C; Yield given. Multistep reaction. Yields of byproduct given;

1: NaOMe View Scheme