1: 44 percent / LDA / tetrahydrofuran; hexane / 1.) -78 deg C, 30 min, 2.) -78 to 0 deg C 2: 98 percent / DIBAL / tetrahydrofuran / -78 °C 3: 10percent aq. HCl / 1,2-dichloro-ethane 4: 78 percent / DMPU, n-BuLi / tetrahydrofuran; hexane / 1.) 0 deg C, 20 min, 2.) -78 deg C, 60 min; -78 to 0 deg C 5: H2 / Rh(PPh3)Cl / benzene / 2 h / 25 °C 6: 5 N aq. NaOH / ethanol / Heating View Scheme

1: 44 percent / LDA / tetrahydrofuran; hexane / 1.) -78 deg C, 30 min, 2.) -78 to 0 deg C 2: 98 percent / DIBAL / tetrahydrofuran / -78 °C 3: 10percent aq. HCl / 1,2-dichloro-ethane 4: 78 percent / DMPU, n-BuLi / tetrahydrofuran; hexane / 1.) 0 deg C, 20 min, 2.) -78 deg C, 60 min; -78 to 0 deg C 5: H2 / Rh(PPh3)Cl / benzene / 2 h / 25 °C 6: 5 N aq. NaOH / ethanol / Heating View Scheme

1: 44 percent / LDA / tetrahydrofuran; hexane / 1.) -78 deg C, 30 min, 2.) -78 to 0 deg C 2: 98 percent / DIBAL / tetrahydrofuran / -78 °C 3: 10percent aq. HCl / 1,2-dichloro-ethane 4: 78 percent / DMPU, n-BuLi / tetrahydrofuran; hexane / 1.) 0 deg C, 20 min, 2.) -78 deg C, 60 min; -78 to 0 deg C 5: H2 / Rh(PPh3)Cl / benzene / 2 h / 25 °C 6: 5 N aq. NaOH / ethanol / Heating View Scheme

1: 90 percent / NaBH4, CeCl3*7H2O / methanol 2: 95 percent / Et3N / CH2Cl2 3: 85 percent / mCPBA / CH2Cl2 4: 90 percent / PTSA / methanol 5: 77 percent / LAH / tetrahydrofuran 6: 95 percent / Et3N / CH2Cl2 8: 88 percent / PTSA / benzene View Scheme