diisobutylaluminium hydride in toluene T=-75°C; 0.833333 h;

in dichloromethane T=20°C; 14 h;

N-ethyl-N,N-diisopropylamine in dichloromethane T=20°C; 16 h;

1.1: 93 percent / K2CO3 / acetonitrile / 19 h / Heating 2.1: 72 percent / NaOMe / methanol / 1.5 h / Heating 3.1: 96 percent / NaBH4 / methanol / 1 h / 20 °C 4.1: 100 percent / Me3SiBr / 0.17 h / 20 °C 5.1: LiHMDS / tetrahydrofuran / 1.25 h / -70 °C 5.2: 86 percent / tetrahydrofuran / 18 h / 0 °C 6.1: 94 percent / H2O2; LiOH / tetrahydrofuran; H2O / 3 h / 20 °C 7.1: NaBH4 / tetrahydrofuran / 0.75 h / 20 °C 7.2: 90 percent / I2 / tetrahydrofuran / 96 h / 20 °C 8.1: 97 percent / NBS; Ph3P / CH2Cl2 / 18 h / 20 °C 9.1: BuLi / hexane / 0.5 h / -75 °C 9.2: 91 percent / tetrahydrofuran / 20 h / -75 - -20 °C 10.1: 90 percent / 1N HCl / acetonitrile / 1.5 h / 20 °C 11.1: 82 percent / Et3N / CH2Cl2 / 20 h / 20 °C View Scheme

1.1: 72 percent / NaOMe / methanol / 1.5 h / Heating 2.1: 96 percent / NaBH4 / methanol / 1 h / 20 °C 3.1: 100 percent / Me3SiBr / 0.17 h / 20 °C 4.1: LiHMDS / tetrahydrofuran / 1.25 h / -70 °C 4.2: 86 percent / tetrahydrofuran / 18 h / 0 °C 5.1: 94 percent / H2O2; LiOH / tetrahydrofuran; H2O / 3 h / 20 °C 6.1: NaBH4 / tetrahydrofuran / 0.75 h / 20 °C 6.2: 90 percent / I2 / tetrahydrofuran / 96 h / 20 °C 7.1: 97 percent / NBS; Ph3P / CH2Cl2 / 18 h / 20 °C 8.1: BuLi / hexane / 0.5 h / -75 °C 8.2: 91 percent / tetrahydrofuran / 20 h / -75 - -20 °C 9.1: 90 percent / 1N HCl / acetonitrile / 1.5 h / 20 °C 10.1: 82 percent / Et3N / CH2Cl2 / 20 h / 20 °C View Scheme

1.1: 96 percent / NaBH4 / methanol / 1 h / 20 °C 2.1: 100 percent / Me3SiBr / 0.17 h / 20 °C 3.1: LiHMDS / tetrahydrofuran / 1.25 h / -70 °C 3.2: 86 percent / tetrahydrofuran / 18 h / 0 °C 4.1: 94 percent / H2O2; LiOH / tetrahydrofuran; H2O / 3 h / 20 °C 5.1: NaBH4 / tetrahydrofuran / 0.75 h / 20 °C 5.2: 90 percent / I2 / tetrahydrofuran / 96 h / 20 °C 6.1: 97 percent / NBS; Ph3P / CH2Cl2 / 18 h / 20 °C 7.1: BuLi / hexane / 0.5 h / -75 °C 7.2: 91 percent / tetrahydrofuran / 20 h / -75 - -20 °C 8.1: 90 percent / 1N HCl / acetonitrile / 1.5 h / 20 °C 9.1: 82 percent / Et3N / CH2Cl2 / 20 h / 20 °C View Scheme

1.1: 97 percent / NBS; Ph3P / CH2Cl2 / 18 h / 20 °C 2.1: BuLi / hexane / 0.5 h / -75 °C 2.2: 91 percent / tetrahydrofuran / 20 h / -75 - -20 °C 3.1: 90 percent / 1N HCl / acetonitrile / 1.5 h / 20 °C 4.1: 82 percent / Et3N / CH2Cl2 / 20 h / 20 °C View Scheme

1.1: NaBH4 / tetrahydrofuran / 0.75 h / 20 °C 1.2: 90 percent / I2 / tetrahydrofuran / 96 h / 20 °C 2.1: 97 percent / NBS; Ph3P / CH2Cl2 / 18 h / 20 °C 3.1: BuLi / hexane / 0.5 h / -75 °C 3.2: 91 percent / tetrahydrofuran / 20 h / -75 - -20 °C 4.1: 90 percent / 1N HCl / acetonitrile / 1.5 h / 20 °C 5.1: 82 percent / Et3N / CH2Cl2 / 20 h / 20 °C View Scheme

1.1: LiHMDS / tetrahydrofuran / 1.25 h / -70 °C 1.2: 86 percent / tetrahydrofuran / 18 h / 0 °C 2.1: 94 percent / H2O2; LiOH / tetrahydrofuran; H2O / 3 h / 20 °C 3.1: NaBH4 / tetrahydrofuran / 0.75 h / 20 °C 3.2: 90 percent / I2 / tetrahydrofuran / 96 h / 20 °C 4.1: 97 percent / NBS; Ph3P / CH2Cl2 / 18 h / 20 °C 5.1: BuLi / hexane / 0.5 h / -75 °C 5.2: 91 percent / tetrahydrofuran / 20 h / -75 - -20 °C 6.1: 90 percent / 1N HCl / acetonitrile / 1.5 h / 20 °C 7.1: 82 percent / Et3N / CH2Cl2 / 20 h / 20 °C View Scheme

1.1: 100 percent / Me3SiBr / 0.17 h / 20 °C 2.1: LiHMDS / tetrahydrofuran / 1.25 h / -70 °C 2.2: 86 percent / tetrahydrofuran / 18 h / 0 °C 3.1: 94 percent / H2O2; LiOH / tetrahydrofuran; H2O / 3 h / 20 °C 4.1: NaBH4 / tetrahydrofuran / 0.75 h / 20 °C 4.2: 90 percent / I2 / tetrahydrofuran / 96 h / 20 °C 5.1: 97 percent / NBS; Ph3P / CH2Cl2 / 18 h / 20 °C 6.1: BuLi / hexane / 0.5 h / -75 °C 6.2: 91 percent / tetrahydrofuran / 20 h / -75 - -20 °C 7.1: 90 percent / 1N HCl / acetonitrile / 1.5 h / 20 °C 8.1: 82 percent / Et3N / CH2Cl2 / 20 h / 20 °C View Scheme