1: 90 percent / Dess-Martin's periodinane / CH2Cl2 / 0.5 h / Ambient temperature 2: 51 percent / nBuLi / diethyl ether; hexane / 1.) 0 deg C, 10 min; 2.) -42 deg C, 135 min 3: 6percent Na(Hg) / methanol; tetrahydrofuran / 3.5 h / -35 °C 4: LiOH / tetrahydrofuran; H2O / 18 h / Ambient temperature 5: Li/NH3(l) / ethanol / 0.5 h / -78 °C View Scheme

1.1: (CH3)3COCl; N(C2H5)3 / diethyl ether / -78 - 0 °C 1.2: 72 percent / tetrahydrofuran; diethyl ether / 8 h / -78 °C 2.1: 72 percent / ((CH3)3Si)2NNa / tetrahydrofuran / 5 h / -78 - -45 °C 3.1: PhCl2(CHPh)(P(C6H11)3)2 / CH2Cl2 / 3 h / Heating 3.2: 98 percent / Pb(OCOCH3)4 / CH2Cl2 4.1: CH3NHOCH3*HCl; (CH3)3Al / tetrahydrofuran / 3 h / 0 °C 4.2: 83 percent / tetrahydrofuran / 8 h / 40 °C 5.1: ((CH3)3Si)2NLi; (C6H5)N(OSO2CF3)2 / tetrahydrofuran; hexamethylphosphoric acid triamide / 0.5 h / -78 °C 5.2: diethyl ether / 1 h / -78 °C 5.3: 75 percent / Li / liquid ammonia; ethanol / 0.17 h / -78 °C 6.1: diisopropyl azodicarboxylate; (C6H5)3P / tetrahydrofuran / 0.5 h / 0 °C 6.2: 67 percent / (NH4)6Mo7O24; H2O2 / ethanol / 3 h / 0 °C 7.1: NaN(Si(CH3)3)2 / tetrahydrofuran; hexamethylphosphoric acid triamide / 3 h / -60 - 0 °C 8.1: LiOH / tetrahydrofuran; H2O / 8 h / 20 °C 8.2: 89 percent / Li / liquid ammonia; ethanol / 0.17 h / -78 °C View Scheme

1.1: ((CH3)3Si)2NLi; (C6H5)N(OSO2CF3)2 / tetrahydrofuran; hexamethylphosphoric acid triamide / 0.5 h / -78 °C 1.2: diethyl ether / 1 h / -78 °C 1.3: 75 percent / Li / liquid ammonia; ethanol / 0.17 h / -78 °C 2.1: diisopropyl azodicarboxylate; (C6H5)3P / tetrahydrofuran / 0.5 h / 0 °C 2.2: 67 percent / (NH4)6Mo7O24; H2O2 / ethanol / 3 h / 0 °C 3.1: NaN(Si(CH3)3)2 / tetrahydrofuran; hexamethylphosphoric acid triamide / 3 h / -60 - 0 °C 4.1: LiOH / tetrahydrofuran; H2O / 8 h / 20 °C 4.2: 89 percent / Li / liquid ammonia; ethanol / 0.17 h / -78 °C View Scheme

1.1: 72 percent / ((CH3)3Si)2NNa / tetrahydrofuran / 5 h / -78 - -45 °C 2.1: PhCl2(CHPh)(P(C6H11)3)2 / CH2Cl2 / 3 h / Heating 2.2: 98 percent / Pb(OCOCH3)4 / CH2Cl2 3.1: CH3NHOCH3*HCl; (CH3)3Al / tetrahydrofuran / 3 h / 0 °C 3.2: 83 percent / tetrahydrofuran / 8 h / 40 °C 4.1: ((CH3)3Si)2NLi; (C6H5)N(OSO2CF3)2 / tetrahydrofuran; hexamethylphosphoric acid triamide / 0.5 h / -78 °C 4.2: diethyl ether / 1 h / -78 °C 4.3: 75 percent / Li / liquid ammonia; ethanol / 0.17 h / -78 °C 5.1: diisopropyl azodicarboxylate; (C6H5)3P / tetrahydrofuran / 0.5 h / 0 °C 5.2: 67 percent / (NH4)6Mo7O24; H2O2 / ethanol / 3 h / 0 °C 6.1: NaN(Si(CH3)3)2 / tetrahydrofuran; hexamethylphosphoric acid triamide / 3 h / -60 - 0 °C 7.1: LiOH / tetrahydrofuran; H2O / 8 h / 20 °C 7.2: 89 percent / Li / liquid ammonia; ethanol / 0.17 h / -78 °C View Scheme

1.1: CH3NHOCH3*HCl; (CH3)3Al / tetrahydrofuran / 3 h / 0 °C 1.2: 83 percent / tetrahydrofuran / 8 h / 40 °C 2.1: ((CH3)3Si)2NLi; (C6H5)N(OSO2CF3)2 / tetrahydrofuran; hexamethylphosphoric acid triamide / 0.5 h / -78 °C 2.2: diethyl ether / 1 h / -78 °C 2.3: 75 percent / Li / liquid ammonia; ethanol / 0.17 h / -78 °C 3.1: diisopropyl azodicarboxylate; (C6H5)3P / tetrahydrofuran / 0.5 h / 0 °C 3.2: 67 percent / (NH4)6Mo7O24; H2O2 / ethanol / 3 h / 0 °C 4.1: NaN(Si(CH3)3)2 / tetrahydrofuran; hexamethylphosphoric acid triamide / 3 h / -60 - 0 °C 5.1: LiOH / tetrahydrofuran; H2O / 8 h / 20 °C 5.2: 89 percent / Li / liquid ammonia; ethanol / 0.17 h / -78 °C View Scheme

1.1: PhCl2(CHPh)(P(C6H11)3)2 / CH2Cl2 / 3 h / Heating 1.2: 98 percent / Pb(OCOCH3)4 / CH2Cl2 2.1: CH3NHOCH3*HCl; (CH3)3Al / tetrahydrofuran / 3 h / 0 °C 2.2: 83 percent / tetrahydrofuran / 8 h / 40 °C 3.1: ((CH3)3Si)2NLi; (C6H5)N(OSO2CF3)2 / tetrahydrofuran; hexamethylphosphoric acid triamide / 0.5 h / -78 °C 3.2: diethyl ether / 1 h / -78 °C 3.3: 75 percent / Li / liquid ammonia; ethanol / 0.17 h / -78 °C 4.1: diisopropyl azodicarboxylate; (C6H5)3P / tetrahydrofuran / 0.5 h / 0 °C 4.2: 67 percent / (NH4)6Mo7O24; H2O2 / ethanol / 3 h / 0 °C 5.1: NaN(Si(CH3)3)2 / tetrahydrofuran; hexamethylphosphoric acid triamide / 3 h / -60 - 0 °C 6.1: LiOH / tetrahydrofuran; H2O / 8 h / 20 °C 6.2: 89 percent / Li / liquid ammonia; ethanol / 0.17 h / -78 °C View Scheme

1.1: NaN(Si(CH3)3)2 / tetrahydrofuran; hexamethylphosphoric acid triamide / 3 h / -60 - 0 °C 2.1: LiOH / tetrahydrofuran; H2O / 8 h / 20 °C 2.2: 89 percent / Li / liquid ammonia; ethanol / 0.17 h / -78 °C View Scheme