hydrogen; Trimethylene glycol in tetrahydrofuran; chloroform T=80°C; P=45003.6 Torr; 72 h;

methyllithium in tetrahydrofuran; diethyl ether T=0 - 20°C; deprotection;

1: tetrahydrofuran / 28 h / -78 - -35 °C 2: 14.7 g / oxalyl chloride; dimethyl sulfoxide; triethylamine / CH2Cl2 / 0.33 h / -55 °C 3: 96 percent / hydrogen bromide; bromine / CH2Cl2; acetic acid / 0.5 h 4: 55 percent / [ReCl(N2)(PMe2Ph)4] / dimethylformamide / 0.67 h / Heating 5: 81 percent / methyllithium / tetrahydrofuran; diethyl ether / 0 - 20 °C View Scheme

1: triethylamine / CH2Cl2 / -55 - 20 °C 2: tetrahydrofuran / 28 h / -78 - -35 °C 3: 14.7 g / oxalyl chloride; dimethyl sulfoxide; triethylamine / CH2Cl2 / 0.33 h / -55 °C 4: 96 percent / hydrogen bromide; bromine / CH2Cl2; acetic acid / 0.5 h 5: 55 percent / [ReCl(N2)(PMe2Ph)4] / dimethylformamide / 0.67 h / Heating 6: 81 percent / methyllithium / tetrahydrofuran; diethyl ether / 0 - 20 °C View Scheme

1: NaOEt, I2 2: p-TsOH / benzene / 8 h / Heating 3: LiAlH4 / tetrahydrofuran / 12 h / Heating 4: 74 percent / H2 / PdO / tetrahydrofuran; CHCl3 / 72 h / 80 °C / 45003.6 Torr View Scheme

1: p-TsOH / benzene / 8 h / Heating 2: LiAlH4 / tetrahydrofuran / 12 h / Heating 3: 74 percent / H2 / PdO / tetrahydrofuran; CHCl3 / 72 h / 80 °C / 45003.6 Torr View Scheme

1: LiAlH4 / tetrahydrofuran / 12 h / Heating 2: 74 percent / H2 / PdO / tetrahydrofuran; CHCl3 / 72 h / 80 °C / 45003.6 Torr View Scheme