1: LiAlH4 2: PBr3 / CH2Cl2 3: LiAlH4 / tetrahydrofuran 4: TiCl4 5: LiAlH4 6: PBr3 / CH2Cl2 7: LiAlH4 / tetrahydrofuran 8: TiCl4 9: LiAlH4 10: PBr3 / CH2Cl2 11: LiAlH4 / tetrahydrofuran 12: TiCl4 13: LiAlH4 14: PBr3 / CH2Cl2 15: LiAlH4 / tetrahydrofuran View Scheme

1: 59 percent / 60 percent NaH / tetrahydrofuran / 1.) 40 deg C, 30 min; 2.) reflux, 30 min 2: 31 percent / I2 / cyclohexane / 3 h / Ambient temperature; Irradiation View Scheme