1: DIBAH / tetrahydrofuran; toluene / 0.5 h / -78 °C 2: 95 percent / imidazole / dimethylformamide / 18 h / Ambient temperature 3: H2 / Lindlar catalyst / methanol / 24 h 4: LiAlH4, TiCl3 / tetrahydrofuran / 1 h / Ambient temperature 5: 80 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / Ambient temperature View Scheme

1: DIBAH / tetrahydrofuran; toluene / 0.5 h / -78 °C 2: 95 percent / imidazole / dimethylformamide / 18 h / Ambient temperature 3: H2 / Lindlar catalyst / methanol / 24 h 4: LiAlH4, TiCl3 / tetrahydrofuran / 1 h / Ambient temperature 5: 80 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / Ambient temperature 6: MnO2 / CH2Cl2 / 2 h / Ambient temperature 7: 80 percent / AgO, NaCN / methanol / 18 h / Ambient temperature View Scheme

1: DIBAH / tetrahydrofuran; toluene / 0.5 h / -78 °C 2: 95 percent / imidazole / dimethylformamide / 18 h / Ambient temperature 3: H2 / Lindlar catalyst / methanol / 24 h 4: LiAlH4, TiCl3 / tetrahydrofuran / 1 h / Ambient temperature 5: 80 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / Ambient temperature 6: MnO2 / CH2Cl2 / 2 h / Ambient temperature View Scheme