potassium carbonate in methanol T=20°C; 0.75 h;

tin(IV) chloride in dichloromethane T=0°C; 28 h; Inert atmosphere; regioselective reaction;

tin(IV) chloride in dichloromethane T=0 - 20°C; 24 h;

1: sodium hydride; tetrabutylammonium iodide / dimethylformamide / 3 h / 20 °C 2: tin(IV) chloride / CH2Cl2 / 24 h / 0 - 20 °C View Scheme

1: sodium hydride; tetrabutylammonium iodide / dimethylformamide / 3 h / 20 °C 2: tin(IV) chloride / CH2Cl2 / 24 h / 0 - 20 °C View Scheme

1: 1.) cc. H2SO4, 2.) NaH / 1.) 4 deg C, 16 h, 2.) DMF, 40 deg C 2: 125.9 g / SnCl4 / CH2Cl2 / 35 h / 3 °C View Scheme

1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 13 h / 0 - 20 °C 2: tin(IV) chloride / dichloromethane / 28 h / 0 °C / Inert atmosphere View Scheme

1: pyridine, 4-(dimethylamino)-pyridine / 17 h 2: 1.) N,O-bis(trimethylsilyl)acetamide, 2.) TfOSiMe3 / 1.) ClCH2CH2Cl, reflux, 10 min, 2.) ClCH2CH2Cl, 70 deg C, 20 h 3: 1,8-diazabicyclo<5.4.0>undec-7-ene / acetonitrile / 10 h 4: 98 percent / 30percent NaOMe / methanol / 3 h / Ambient temperature 5: 98 percent / NaH / tetrahydrofuran / 40 - 70 °C 6: H2 / 5percent Pd/C / tetrahydrofuran / Ambient temperature 7: 30percent NaOMe / methanol / Ambient temperature; pH 11 8: 84 percent / H2, NaOAc / 5percent Pd/C / methanol / 45 °C / 2250.2 Torr View Scheme

1: Dess-Martin periodinane / CH2Cl2 / 72 h / 20 °C 2: 16.7 g / diethyl ether / 7 h / -30 - -15 °C View Scheme

Dess-Martin periodane in dichloromethane T=20°C; 48 h;