1: 85 percent / TsOH*H2O / benzene / 43 h / Heating; azeotropic removal of water 2: 1.) n-BuLi, 2.) / 1.) THF, -78 deg C, 2.) -78 deg C 3: DIBAL / toluene / 7 h / -78 °C 4: oxalic acid / CH2Cl2; H2O / 3.5 h / Ambient temperature 5: 78 percent / imidazole / dimethylformamide / 65 h / Ambient temperature View Scheme

1: 85 percent / TsOH*H2O / benzene / 43 h / Heating; azeotropic removal of water 2: 1.) n-BuLi, 2.) / 1.) THF, -78 deg C, 2.) -78 deg C 3: DIBAL / toluene / 7 h / -78 °C 4: oxalic acid / CH2Cl2; H2O / 3.5 h / Ambient temperature 5: 78 percent / imidazole / dimethylformamide / 65 h / Ambient temperature 6: 1.) OsO4, 2.) aq. NaHSO3 / 1.) a) pyridine, 0-5 deg C, b) RT, 5 h, 2.) pyridine, RT, 3 h 7: 53 percent / SeO2 / 2-methyl-propan-2-ol; benzene / Heating 8: 96 percent / acetic acid (glacial) / tetrahydrofuran; H2O / 80 h / Ambient temperature View Scheme

1: 85 percent / TsOH*H2O / benzene / 43 h / Heating; azeotropic removal of water 2: 1.) n-BuLi, 2.) / 1.) THF, -78 deg C, 2.) -78 deg C 3: DIBAL / toluene / 7 h / -78 °C 4: oxalic acid / CH2Cl2; H2O / 3.5 h / Ambient temperature 5: 78 percent / imidazole / dimethylformamide / 65 h / Ambient temperature 6: 1.) OsO4, 2.) aq. NaHSO3 / 1.) a) pyridine, 0-5 deg C, b) RT, 5 h, 2.) pyridine, RT, 3 h 7: 94 percent / pyridine / 10 h / 4 °C 8: 67 percent / SeO2 / 2-methyl-propan-2-ol; benzene / Heating 9: 88 percent / acetic acid (glacial) / tetrahydrofuran; H2O / 162 h / Ambient temperature View Scheme

Yield given. Multistep reaction. Yields of byproduct given;

2,6-dimethylpyridine; palladium diacetate; 1,3-bis-(diphenylphosphino)propane in tetrahydrofuran T=60°C; P=38787.1 Torr; 48 h;

1: 83 percent Turnov. / p-toluenesulfonic acid / benzene / 4.5 h / Heating 2: n-BuLi / 1.) -70 deg C., ether, hexane; 2.) room temp 3: 2.) KF*2H2O / 1) Irradiation 2) DMSO, 9 hr. room temp View Scheme

1: 85 percent / TsOH*H2O / benzene / 43 h / Heating; azeotropic removal of water View Scheme

tetrakis(triphenylphosphine) palladium(0); sodium carbonate in water; toluene Suzuki coupling; Reflux;

triethylamine in methanol T=37°C; 24 h;