N-iodo-succinimide; pyridinium p-toluenesulfonate in ethylene glycol dimethyl ether T=-5 - 0°C; 3 h;

trimethylsilyl iodide in water; acetonitrile T=-15 - -7°C; 40.5 h; Inert atmosphere; Reagent/catalystTemperatureTime;

chloro-trimethyl-silane; sodium iodide in dichloromethane; water T=25°C; 0.333333 h; Inert atmosphere; ConcentrationTime;

1: tBuCOCl / tetrahydrofuran / 0 - 10 °C 2: TsOH*H2O / methanol / 50 °C 3: tetrahydrofuran / 20 - 35 °C 4: 91 percent / CuCl; iPr2NEt; Celite / toluene; acetonitrile / 0.5 h / 80 °C 5: LHMDS / tetrahydrofuran / -10 °C 6: TMSCl; NaI / H2O; CH2Cl2 / 0.33 h / 20 - 25 °C View Scheme

1: LHMDS / tetrahydrofuran / -10 °C 2: TMSCl; NaI / H2O; CH2Cl2 / 0.33 h / 20 - 25 °C View Scheme

1: 91 percent / Me3Al; Ph3PO / toluene / 25 °C 2: 92 percent / KN(TMS)2 / tetrahydrofuran / -20 °C 3: 75 percent / TMSCl / H2O; CH2Cl2 View Scheme

1: 81 percent / Ph3P / CCl4; triethylamine / 12 h / 20 °C 2: 91 percent / Me3Al; Ph3PO / toluene / 25 °C 3: 92 percent / KN(TMS)2 / tetrahydrofuran / -20 °C 4: 75 percent / TMSCl / H2O; CH2Cl2 View Scheme

1.1: LHMDS / tetrahydrofuran / -15 °C 2.1: BnMe3NOH; NaOH / dioxane / 45 °C 2.2: aq. HCl / 50 °C 3.1: tBuCOCl / tetrahydrofuran / 0 - 10 °C 4.1: TsOH*H2O / methanol / 50 °C 5.1: tetrahydrofuran / 20 - 35 °C 6.1: 91 percent / CuCl; iPr2NEt; Celite / toluene; acetonitrile / 0.5 h / 80 °C 7.1: LHMDS / tetrahydrofuran / -10 °C 8.1: TMSCl; NaI / H2O; CH2Cl2 / 0.33 h / 20 - 25 °C View Scheme

1.1: LHMDS / tetrahydrofuran / -15 °C 2.1: BnMe3NOH; NaOH / dioxane / 45 °C 2.2: aq. HCl / 50 °C 3.1: tBuCOCl / tetrahydrofuran / 0 - 10 °C 4.1: TsOH*H2O / methanol / 50 °C 5.1: tetrahydrofuran / 20 - 35 °C 6.1: 91 percent / CuCl; iPr2NEt; Celite / toluene; acetonitrile / 0.5 h / 80 °C 7.1: LHMDS / tetrahydrofuran / -10 °C 8.1: TMSCl; NaI / H2O; CH2Cl2 / 0.33 h / 20 - 25 °C View Scheme

1.1: BnMe3NOH; NaOH / dioxane / 45 °C 1.2: aq. HCl / 50 °C 2.1: tBuCOCl / tetrahydrofuran / 0 - 10 °C 3.1: TsOH*H2O / methanol / 50 °C 4.1: tetrahydrofuran / 20 - 35 °C 5.1: 91 percent / CuCl; iPr2NEt; Celite / toluene; acetonitrile / 0.5 h / 80 °C 6.1: LHMDS / tetrahydrofuran / -10 °C 7.1: TMSCl; NaI / H2O; CH2Cl2 / 0.33 h / 20 - 25 °C View Scheme