1: 1.) Mg, I2 / 1.) anhydrous THF, 4 h, 60 deg C, 2.) THF 2: 97 percent / H2O, 10percent HCl / methanol / 1 h / Ambient temperature 3: 1.) t-BuOK / 1.) anhydrous THF, 30 min, RT, 2.) THF, RT, 24 h 4: 58 percent / LAH / diethyl ether / 6 h / -78 °C 5: 93 percent / m-CPBA (80 percent) / CH2Cl2 / 0.67 h / 0 °C 6: 97 percent / H2, 1M NaOH / 10percent Pd/C / ethanol / 6 h / -60 °C 7: 89 percent / LiBr, NCS / methanol / 1 h / Ambient temperature 8: 79 percent / TsOH / 5 h / Ambient temperature 9: 1.) t-BuLi / 1.) Et2O, hexane, -78 deg C, 1.75 h, 2.) Et2O, hexane, RT 10: 93 percent / H2O, 5percent HCl / methanol / RT, 8 h, then -20 deg C, 16 h 11: 72 percent / RuCl3*H2O, NaIO4 / CCl4; acetonitrile; H2O / 1.25 h / Ambient temperature View Scheme

1.1: t-BuLi / tetrahydrofuran / 0.5 h / -76 °C 1.2: S / tetrahydrofuran / 3 h / -76 - 20 °C 1.3: tetrahydrofuran / 0.25 h / 20 °C 2.1: aq. HCl / acetone / 2 h / Heating View Scheme

bis-triphenylphosphine-palladium(II) chloride; n-butyllithium; diisobutylaluminium hydride; zinc(II) chloride 1.) THF-hexane, -78 deg C, then 25 deg C, 1 h, 2.) 25 deg C, 14 h; Yield given. Multistep reaction;

1: 1.) Mg, I2 / 1.) anhydrous THF, 4 h, 60 deg C, 2.) THF 2: 97 percent / H2O, 10percent HCl / methanol / 1 h / Ambient temperature 3: 1.) t-BuOK / 1.) anhydrous THF, 30 min, RT, 2.) THF, RT, 24 h 4: 58 percent / LAH / diethyl ether / 6 h / -78 °C 5: 1.) (L)-(+)-diisopropyl tartrate, 4A sieves, Ti(OiPr)4, t-BuOOH / 1.) CH2Cl2, 1 h, 2.) CH2Cl2, -20 deg C, 3.5 h 6: H2, 1M NaOH / 10percent Pd/C / ethanol / Ambient temperature 7: LiBr, NCS / methanol / Ambient temperature 8: TsOH / Ambient temperature 9: 1.) t-BuLi / 1.) Et2O, hexane, -78 deg C, 2.) Et2O, hexane, RT 10: H2O, 5percent HCl / methanol / RT, then -20 deg C 11: RuCl3*H2O, NaIO4 / CCl4; acetonitrile; H2O / Ambient temperature View Scheme

toluene-4-sulfonic acid in benzene Heating / refluxwater separator;

lithium boron tetrafluoride in ethylene glycol T=95°C; 3.5 h; Inert atmosphere;

toluene-4-sulfonic acid in ethylene glycol; benzene

1.1: t-BuLi / tetrahydrofuran / 0.5 h / -76 °C 1.2: Se / tetrahydrofuran / 3 h / -76 - 20 °C 1.3: tetrahydrofuran / 0.25 h / 20 °C 2.1: aq. HCl / acetone / 2 h / Heating View Scheme

1.1: t-BuLi / tetrahydrofuran / 0.5 h / -76 °C 1.2: tetrahydrofuran / 2 h / -76 - 20 °C 2.1: aq. HCl / acetone / 2 h / Heating View Scheme

1.1: Mg / tetrahydrofuran 1.2: 86 percent / tetrahydrofuran / 2 h / 40 °C 2.1: 64 percent / 4-toluenesulphonic acid / tetrahydrofuran; H2O / Heating 3.1: 2 h / Heating 4.1: 94 percent / N2H4*H2O / ethanol / 3 h / Heating View Scheme