1: 91 percent / H2, ethylenediamine / P2Ni / ethanol / slight positive pressure 2: 7.5 g / pyridine / 2 h / 0 - 5 °C 3: 1.) -70 deg C, Di-Li-CuCl4, 2.) a) THF, 3 h to rt, b) 1 h View Scheme

1.1: 91 percent / I2; imidazole; PPh3 / toluene / 2 h / 20 °C 2.1: 99 percent / acetonitrile / 16 h / Heating 3.1: KN(SiMe3)2 / toluene; tetrahydrofuran / 2 h / -78 - 0 °C 3.2: 95 percent / HMPA / tetrahydrofuran; toluene / 16 h / -78 - -5 °C 4.1: AD-mix-β; MeSO2NH2 / 2-methyl-propan-2-ol; H2O / 16 h / 0 °C 5.1: KOH / H2O; methanol / 60 °C 6.1: 2.12 g / TsOH / CH2Cl2 / 0.5 h / 20 °C 7.1: 68 percent / Re2O7; 2,6-lutidine / CH2Cl2 / 8 h / 20 °C 8.1: 92 percent / H2; Et3N / Lindlar catalyst / hexane; various solvent(s) / 16 h / -10 - -4 °C 9.1: 71 percent / Et3N / CH2Cl2 / 1 h / 0 °C 10.1: 92 percent / AD-mix-β; MeSO2NH2 / 2-methyl-propan-2-ol; H2O / 0 °C 11.1: 81 percent / pyridine / 3 h / Heating 12.1: 100 percent / LiAlH4 / diethyl ether / 2 h / Heating 13.1: diisopropylethylamine; DMAP / CH2Cl2 / 6 h / 20 °C 14.1: 508 mg / diisopropylethylamine / CH2Cl2 / 12 h 15.1: 95 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C 16.1: 86 percent / I2; Ph3P; imidazole / CH2Cl2 / 1 h / 20 °C 17.1: 85 percent / NaHCO3 / acetonitrile / 36 h / 40 °C 18.1: BuLi / hexane; tetrahydrofuran / 0.25 h / cooling 18.2: 60 percent / tetrahydrofuran; hexane / 0.25 h 19.1: 98 percent / H2 / chlorotris(triphenylphosphine)rhodium(I) / benzene; ethanol / 12 h 20.1: 83 percent / AcCl / methanol; CH2Cl2 / 2 h / 20 °C View Scheme

hydrogen; ethylenediamine; P2Ni in ethanol slight positive pressure;