1: NEt3 / CH2Cl2 / 0.5 h / 0 °C 2: NaI / acetone / 10 h / Heating 3: Li2CuCl4 / tetrahydrofuran / 0.5 h / 25 °C 4: pyridinium p-toluenesulfonate / ethanol / 3.5 h / 40 °C 5: 1.) sodium hydride / 1.) DME, 50 deg C to 55 deg C, 2 h, 2.) toluene, -10 deg C, 2 h 6: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 0.5 h, 2.) -78 deg C, 2 h View Scheme

1: oxalyl chloride; DMSO; triethylamine / CH2Cl2 / -60 - 20 °C 2: tetrahydrofuran / 20 °C 3: PPTS / ethanol / 60 °C View Scheme

titanium tetrachloride in dichloromethane T=0 - 25°C; Acetylation; 6 h;

water; β-cyclodextrin in methanol T=50°C; 10 h;

1: 94 percent / Et3N / CH2Cl2 / 0.5 h / 0 °C 2: 2. H2O / 1. benzene, DMF, 16h reflux 3: 60 percent / NaOH / methanol / a) 24h b) H2O, 0 deg C, HCl 4: 90 percent / hexamethylphosphoric acid triamide / 3 h / 180 °C 5: 90 percent / LiAlH4 / diethyl ether / a. reflux while adding reagent b. overnight room temperature c. reflux, 3h 6: 70 percent / pyridinium chlorochromate, NaOAc / CH2Cl2 / 3 h / Ambient temperature View Scheme

cerium(III) chloride; sodium iodide in acetonitrile deallylation; 5.5 h; Heating;

benzyltriphenylphosphonium tribromide in dichloromethane T=20°C; 0.133333 h;

tetra-n-butylammonium tribromide in methanol 0.3 h;

[BMIm][HSO4] in hexane microwave irradiation;

tris(triphenylphosphine)ruthenium(II) chloride in 1,4-dioxane T=180°C; 5 h;