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

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

1: 2. H2O / 1. benzene, DMF, 16h reflux 2: 60 percent / NaOH / methanol / a) 24h b) H2O, 0 deg C, HCl 3: 90 percent / hexamethylphosphoric acid triamide / 3 h / 180 °C 4: 90 percent / LiAlH4 / diethyl ether / a. reflux while adding reagent b. overnight room temperature c. reflux, 3h 5: 70 percent / pyridinium chlorochromate, NaOAc / CH2Cl2 / 3 h / Ambient temperature 6: 70 percent / Mg / tetrahydrofuran / a. ice-cooled solution, 10 min b. overnight room temperature c. 3h reflux 7: 50 percent / mercuric acetate / 16 h / Heating 8: 80 percent / 0.58 h / 180 °C / sealed tube 9: 90 percent / LiAlH4 / diethyl ether / a. reflux while adding reagent b. overnight room temperature c. 1h reflux 10: Et3N / CH2Cl2 / 0 °C 11: 1.) cuprous iodide / 1.) Et2O, -10 deg C, 1o min 2. 4h, 0 deg C 12: 80 percent / PTS / methanol / 4 h View Scheme

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

1: 2. H2O / 1. benzene, DMF, 16h reflux 2: 60 percent / NaOH / methanol / a) 24h b) H2O, 0 deg C, HCl 3: 90 percent / hexamethylphosphoric acid triamide / 3 h / 180 °C 4: 90 percent / LiAlH4 / diethyl ether / a. reflux while adding reagent b. overnight room temperature c. reflux, 3h 5: 70 percent / pyridinium chlorochromate, NaOAc / CH2Cl2 / 3 h / Ambient temperature 6: 70 percent / Mg / tetrahydrofuran / a. ice-cooled solution, 10 min b. overnight room temperature c. 3h reflux 7: 50 percent / mercuric acetate / 16 h / Heating 8: 80 percent / 0.58 h / 180 °C / sealed tube 9: 90 percent / LiAlH4 / diethyl ether / a. reflux while adding reagent b. overnight room temperature c. 1h reflux 10: Et3N / CH2Cl2 / 0 °C 11: 1.) cuprous iodide / 1.) Et2O, -10 deg C, 1o min 2. 4h, 0 deg C View Scheme