1: 94 percent / LiAlH4 / diethyl ether / 0.33 h / -78 °C 2: 91 percent / (COCl)2, DMSO, TEA / CH2Cl2 3: 86 percent / KOt-Bu / tetrahydrofuran / 0.33 h / -78 deg C --> 0 deg C 4: 100 percent / DIBAL-H / CH2Cl2 / 0.25 h / -78 °C 5: 82 percent / NBS, PPh3, 2-methyl-2-butene / CH2Cl2 / 0.33 h / -78 deg C to 0 deg C 6: tetrahydrofuran / 0.33 h / 0 °C 7: NaIO4 / various solvent(s); H2O / 0 °C View Scheme

1: 86 percent / KOt-Bu / tetrahydrofuran / 0.33 h / -78 deg C --> 0 deg C 2: 100 percent / DIBAL-H / CH2Cl2 / 0.25 h / -78 °C 3: 82 percent / NBS, PPh3, 2-methyl-2-butene / CH2Cl2 / 0.33 h / -78 deg C to 0 deg C 4: tetrahydrofuran / 0.33 h / 0 °C 5: NaIO4 / various solvent(s); H2O / 0 °C View Scheme

1: 91 percent / (COCl)2, DMSO, TEA / CH2Cl2 2: 86 percent / KOt-Bu / tetrahydrofuran / 0.33 h / -78 deg C --> 0 deg C 3: 100 percent / DIBAL-H / CH2Cl2 / 0.25 h / -78 °C 4: 82 percent / NBS, PPh3, 2-methyl-2-butene / CH2Cl2 / 0.33 h / -78 deg C to 0 deg C 5: tetrahydrofuran / 0.33 h / 0 °C 6: NaIO4 / various solvent(s); H2O / 0 °C View Scheme