1: 1.) ethylmagnesium bromide / 1.) THF, room temperature, 1 h, 2.) 15 min 2: 75 percent / DIBAH / tetrahydrofuran; toluene / 0.5 h / -78 °C 3: 90 percent / H2 / Lindlar catalyst / methanol / 24 h 4: 80 percent / imidazole / dimethylformamide / 18 h / Ambient temperature 5: 90 percent / LiAlH4, TiCl3 / tetrahydrofuran / 0.5 h / Ambient temperature 6: sodium fluoride, pyridinium fluoride / tetrahydrofuran; acetonitrile / 5 h / Ambient temperature 7: MnO2 / CCl4 / 0.5 h 8: 60 percent / NaCN, AgO, MnO2 / 14 h / 40 °C 9: 70 percent / 6 M NaOH / ethanol / 50 °C View Scheme

1: 1.) ethylmagnesium bromide / 1.) THF, room temperature, 1 h, 2.) 15 min 2: 75 percent / DIBAH / tetrahydrofuran; toluene / 0.5 h / -78 °C 3: 90 percent / H2 / Lindlar catalyst / methanol / 24 h 4: 80 percent / imidazole / dimethylformamide / 18 h / Ambient temperature 5: 90 percent / LiAlH4, TiCl3 / tetrahydrofuran / 0.5 h / Ambient temperature 6: sodium fluoride, pyridinium fluoride / tetrahydrofuran; acetonitrile / 5 h / Ambient temperature 7: MnO2 / CCl4 / 0.5 h View Scheme

Multi-step reaction with 5 steps 1: 1.) ethylmagnesium bromide / 1.) THF, room temperature, 1 h, 2.) 15 min2: 75 percent / DIBAH / tetrahydrofuran; toluene / 0.5 h / -78 °C3: 90 percent / H2 / Lindlar catalyst / methanol / 24 h4: 80 percent / imidazole / dimethylformamide / 18 h / Ambient temperature5: 90 percent / LiAlH4, TiCl3 / tetrahydrofuran / 0.5 h / Ambient temperature  

Multi-step reaction with 4 steps 1: 1.) ethylmagnesium bromide / 1.) THF, room temperature, 1 h, 2.) 15 min2: 75 percent / DIBAH / tetrahydrofuran; toluene / 0.5 h / -78 °C3: 90 percent / H2 / Lindlar catalyst / methanol / 24 h4: 80 percent / imidazole / dimethylformamide / 18 h / Ambient temperature  

Multi-step reaction with 2 steps 1: 1.) ethylmagnesium bromide / 1.) THF, room temperature, 1 h, 2.) 15 min2: 75 percent / DIBAH / tetrahydrofuran; toluene / 0.5 h / -78 °C