pyridinium hydrobromide perbromide in methanol 15 h; Ambient temperature;

1.1: (n-Bu)2BOTf; Et3N / CH2Cl2 / 1.33 h / -78 - 0 °C 1.2: CH2Cl2 / 2 h / -78 - 0 °C 1.3: H2O2 / CH2Cl2; aq. phosphate buffer / 20 °C / pH 7.2 2.1: 3.11 g / 2,6-lutidine / CH2Cl2 / 1 h / 20 °C 3.1: 77 percent / NaBH4 / tetrahydrofuran; H2O / 16 h / 25 °C 4.1: 81 percent / pyridine / CH2Cl2 / 1 h / 20 °C 5.1: 44 percent / (Me3Si)3SiH; AIBN / benzene / 4 h / Heating 6.1: 90 percent / AcOH; (n-Bu)4NF / tetrahydrofuran / 336 h / 20 °C View Scheme

1: diisobutylaluminium hydride / tetrahydrofuran; toluene / 48 h / 20 °C / Cooling with ice; Inert atmosphere 2: pyridine / 18 h / Inert atmosphere 3: hydrogenchloride; water / ethanol / 18 h / 20 °C / Inert atmosphere View Scheme

CH3O3S(1-)*C27H53N2O12(1+); cesium fluoride in 1,1-dimethylpropan-1-ol T=70°C; 0.25 h; chemoselective reaction;

perchloric acid immobilized on silica gel in dichloromethane 16 h;

1.1: (n-Bu)2BOTf; Et3N / CH2Cl2 / 1.33 h / -78 - 0 °C 1.2: CH2Cl2 / 2 h / -78 - 0 °C 1.3: H2O2 / CH2Cl2; aq. phosphate buffer / 20 °C / pH 7.2 2.1: 3.11 g / 2,6-lutidine / CH2Cl2 / 1 h / 20 °C 3.1: 77 percent / NaBH4 / tetrahydrofuran; H2O / 16 h / 25 °C 4.1: 81 percent / pyridine / CH2Cl2 / 1 h / 20 °C 5.1: 44 percent / (Me3Si)3SiH; AIBN / benzene / 4 h / Heating 6.1: 90 percent / AcOH; (n-Bu)4NF / tetrahydrofuran / 336 h / 20 °C 7.1: 78 percent / H2; HClO4 / Pd/C / ethanol / 48 h / 3040 Torr View Scheme

N-chloro-succinimide; magnesium 1.) C6H6, THF, 10 min, 2.) C6H6, THF, a) 0 deg C, 5 min, b) RT, 25 min; Yield given. Multistep reaction;

1.1: n-BuLi / tetrahydrofuran; hexane / 2 h / -78 °C 1.2: 35 percent / tetrahydrofuran; hexane / 20 °C 2.1: 88 percent / TBAF / tetrahydrofuran / 0.75 h View Scheme

sodium hydride in tetrahydrofuran T=0°C; Wittig reaction;

1: 25 percent / NaH / tetrahydrofuran / 0 °C 2: 80 percent / TBAF / tetrahydrofuran; diethyl ether / 20 h / 0 °C View Scheme