1: 95 percent / PPA / 1 h / 120 °C 2: 82 percent / DIBAL-H / toluene / 2 h / -78 °C 3: 98 percent / POCl3 / triethylamine / 1.) RT, 3 h, 2.) reflux, 1 h 4: 1.) NaBH4, 2.) NaBH4, 3.) NH3, 4.) Li, 5.) Jones reagent View Scheme

1: 95 percent / PPA / 1 h / 120 °C 2: 82 percent / DIBAL-H / toluene / 2 h / -78 °C 3: 98 percent / POCl3 / triethylamine / 1.) RT, 3 h, 2.) reflux, 1 h 4: 1.) NaBH4, 2.) NaBH4, 3.) NH3, 4.) Li, 5.) Jones reagent 5: 68 percent / pyridinium bromide perbromide / tetrahydrofuran / 0.5 h 6: 70 percent / LiBr, LiCO3 / dimethylformamide / 1 h / Heating View Scheme