1: 85 percent / DIBAL-H / CH2Cl2 / -78 °C 2: 100 percent / H2 / Pd/C / ethanol 3: 64 percent / PBr3 / diethyl ether / 0 °C View Scheme

tetraethylammonium p-toluenesulfonate in acetonitrile T=20°C; Electrolysis;

1.1: NaOMe / methanol / 3 h / 63 - 66 °C 2.1: 89.7 percent / H2 / Raney-Co / toluene; methanol / 1 h / 90 - 100 °C / 9880 - 12160 Torr 3.1: NaOMe / toluene / 0.5 h / 70 - 80 °C 4.1: LiAlH4 / toluene; tetrahydrofuran / 2 h / 73 - 75 °C 4.2: via salt with L-o-chlorotartranilic acid/Celite 5.1: aq. NaOH / toluene / 2 h / 45 - 55 °C 6.1: Et3N / toluene / 1.25 h / 22 - 25 °C 7.1: NaOMe / toluene / 5.5 h / Heating 8.1: HCl / propan-2-ol / 2.5 h / 71 - 75 °C View Scheme

1.1: NaOMe / methanol / 3 h / 63 - 66 °C 2.1: 89.7 percent / H2 / Raney-Co / toluene; methanol / 1 h / 90 - 100 °C / 9880 - 12160 Torr 3.1: NaOMe / toluene / 0.5 h / 70 - 80 °C 4.1: LiAlH4 / toluene; tetrahydrofuran / 2 h / 73 - 75 °C 4.2: via salt with L-o-chlorotartranilic acid/Celite 5.1: aq. NaOH / toluene / 2 h / 45 - 55 °C View Scheme

1.1: NaOMe / methanol / 3 h / 63 - 66 °C 2.1: 89.7 percent / H2 / Raney-Co / toluene; methanol / 1 h / 90 - 100 °C / 9880 - 12160 Torr 3.1: NaOMe / toluene / 0.5 h / 70 - 80 °C 4.1: LiAlH4 / toluene; tetrahydrofuran / 2 h / 73 - 75 °C 4.2: via salt with L-o-chlorotartranilic acid/Celite View Scheme

1: 85 percent / DIBAL-H / CH2Cl2 / -78 °C 2: 100 percent / H2 / Pd/C / ethanol View Scheme