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

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

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

copper(l) iodide 1.) Et2O, -10 deg C, 1o min 2. 4h, 0 deg C; Yield given. Multistep reaction;

hydrogenchloride in methanol T=4°C;