1: LiAlH4 / diethyl ether / 1 h / 0 °C 2: p-toluenesulfonic acid / methanol; H2O / 3 h / Heating View Scheme

1: 2.) PCC 2: n-BuLi / toluene / 2 h / 25 °C 3: lithium aluminium hydride / tetrahydrofuran / 4 h / Heating View Scheme

1: 90 percent / acetonitrile / 24 h / Heating 2: NaOEt / tetrahydrofuran / 1 h / 25 °C 3: n-BuLi / toluene / 2 h / 25 °C 4: lithium aluminium hydride / tetrahydrofuran / 4 h / Heating View Scheme

1: n-BuLi / toluene / 2 h / 25 °C 2: lithium aluminium hydride / tetrahydrofuran / 4 h / Heating View Scheme

1: n-BuLi / toluene / 2 h / 25 °C 2: lithium aluminium hydride / tetrahydrofuran / 4 h / Heating View Scheme

1: NaOEt / tetrahydrofuran / 1 h / 25 °C 2: n-BuLi / toluene / 2 h / 25 °C 3: lithium aluminium hydride / tetrahydrofuran / 4 h / Heating View Scheme

1: Baeyer-Villiger oxidation 2: 2.) PCC 3: n-BuLi / toluene / 2 h / 25 °C 4: lithium aluminium hydride / tetrahydrofuran / 4 h / Heating View Scheme

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 7: 70 percent / Mg / tetrahydrofuran / a. ice-cooled solution, 10 min b. overnight room temperature c. 3h reflux 8: 50 percent / mercuric acetate / 16 h / Heating 9: 80 percent / 0.58 h / 180 °C / sealed tube 10: 90 percent / LiAlH4 / diethyl ether / a. reflux while adding reagent b. overnight room temperature c. 1h reflux 11: Et3N / CH2Cl2 / 0 °C 12: 1.) cuprous iodide / 1.) Et2O, -10 deg C, 1o min 2. 4h, 0 deg C 13: 80 percent / PTS / methanol / 4 h View Scheme

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

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