1: 99 percent / Et3N; DMAP 2: 82 percent / TBAF View Scheme

sodium tetrahydroborate; hydrogen; [Ni(O2CCH3)2]*4H2O in ethanol T=20°C; P=10343.2 Torr; 4 h; AutoclaveInert atmosphereLarge scale;

5 Pt/Al2O3; hydrogen Reagent/catalyst;

1.1: DMAP / dimethylformamide / 20 h / 100 °C 2.1: tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C 3.1: 84 percent / diisopropylethylamine; methanesulfonyl chloride / CH2Cl2 / 3 h / 0 °C 4.1: NaH / tetrahydrofuran / 0 - 20 °C 4.2: 72 percent / tetrahydrofuran / 19 h / 75 °C 5.1: 80 percent / LiI / dimethylformamide / 17 h / 130 °C 6.1: 39 percent / p-toluenesulfonic acid / methanol / 1.25 h / 20 °C View Scheme

1.1: 81 percent / triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 18 h / 20 - 40 °C 2.1: 85 percent / NaOMe; MeOH / 24 h / 20 °C 3.1: 99 percent / diisopropylethylamine; methanesulfonyl chloride / CH2Cl2 / 3 h / 0 °C 4.1: NaH / tetrahydrofuran / 0 - 20 °C 4.2: 75 percent / tetrahydrofuran / 19 h / 75 °C 5.1: 74 percent / LiI / dimethylformamide / 17 h / 130 °C 6.1: 59 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C View Scheme

1.1: DMAP / dimethylformamide / 20 h / 100 °C 2.1: tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C 3.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 18 h / 20 - 40 °C 4.1: NaOMe; MeOH / 24 h / 20 °C 5.1: 93 percent / diisopropylethylamine; methanesulfonyl chloride / CH2Cl2 / 3 h / 0 °C 6.1: NaH / tetrahydrofuran / 0 - 20 °C 6.2: 74 percent / tetrahydrofuran / 19 h / 75 °C 7.1: 63 percent / LiI / dimethylformamide / 17 h / 130 °C 8.1: 54 percent / p-toluenesulfonic acid / methanol / 1.25 h / 20 °C View Scheme