diisobutylaluminium hydride in dichloromethane T=-91°C; Reduction;

1.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / 20 °C 1.2: 79 percent / tetrahydrofuran; hexane / 2 h / 20 °C 2.1: 9-borabicyclo[3.3.1]nonane / tetrahydrofuran / 15 h / 20 °C 2.2: 99 percent / NaOH; H2O2 / tetrahydrofuran; H2O / 6 h / 20 °C 3.1: 95 percent / triphenylphosphine; diethyl azodicarboxylate / tetrahydrofuran / 4 h / 20 °C 4.1: hydrazine hydrate / ethanol / 3 h / Heating 5.1: 5.06 g / NaHCO3 / ethanol; CH2Cl2; H2O / 0.5 h / 20 °C 6.1: 78 percent / p-toluenesulfonic acid / toluene / 1 h / Heating 7.1: N-methylmorpholine N-oxide; osmium tetraoxide / tetrahydrofuran; acetone; H2O / 14 h / 20 °C 8.1: 234 mg / sodium periodate / tetrahydrofuran; methanol; H2O / 3 h / 20 °C 9.1: 48 percent / sodium cyanide; manganese(IV) oxide / 0.5 h / 20 °C View Scheme