Dess-Martin periodane in dichloromethane T=20°C; 30 h;

1.1: KHMDS / tetrahydrofuran; toluene / 1 h / -78 °C 1.2: 90 percent / tetrahydrofuran; toluene / 2.25 h / -78 - 0 °C 2.1: 92 percent / aq. AcOH / 20 h / 20 °C 3.1: NaIO4; SiO2 / CH2Cl2; H2O / 0.5 h / 20 °C 3.2: KHMDS / tetrahydrofuran; toluene / 1 h / -78 °C 3.3: 50 percent / tetrahydrofuran; toluene; CH2Cl2 / 4 h / 20 °C 4.1: 88 percent / Dess-Martin periodinane / CH2Cl2 / 30 h / 20 °C View Scheme

1.1: NaIO4; SiO2 / CH2Cl2; H2O / 0.5 h / 20 °C 1.2: KHMDS / tetrahydrofuran; toluene / 1 h / -78 °C 1.3: 50 percent / tetrahydrofuran; toluene; CH2Cl2 / 4 h / 20 °C 2.1: 88 percent / Dess-Martin periodinane / CH2Cl2 / 30 h / 20 °C View Scheme

1.1: 92 percent / aq. AcOH / 20 h / 20 °C 2.1: NaIO4; SiO2 / CH2Cl2; H2O / 0.5 h / 20 °C 2.2: KHMDS / tetrahydrofuran; toluene / 1 h / -78 °C 2.3: 50 percent / tetrahydrofuran; toluene; CH2Cl2 / 4 h / 20 °C 3.1: 88 percent / Dess-Martin periodinane / CH2Cl2 / 30 h / 20 °C View Scheme

1.1: EtMgBr; CuCl / diethyl ether / 2 h / 20 °C 1.2: 28 percent / diethyl ether / 24 h / Heating 2.1: H2 / Lindlar's catalyst / methanol / 20 °C 3.1: 80 percent / MnO2 / hexane / 0.5 h View Scheme

1.1: 67 percent / PBr3; pyridine / diethyl ether / 2 h / 20 °C 2.1: EtMgBr; CuCl / diethyl ether / 2 h / 20 °C 2.2: 28 percent / diethyl ether / 24 h / Heating 3.1: H2 / Lindlar's catalyst / methanol / 20 °C 4.1: 80 percent / MnO2 / hexane / 0.5 h View Scheme

1: H2 / Lindlar's catalyst / methanol / 20 °C 2: 80 percent / MnO2 / hexane / 0.5 h View Scheme