1: With oxygen T=-78°C; 2: With dimethylsulfide

1.1: 88 percent / KOH / tetrahydrofuran / 18 h / 0 °C 2.1: 90 percent / dimethylsulfoxide 3.1: 82 percent / aq. NaOH / methanol / Heating 4.1: 92 percent / Me3SiCl / 20 °C 5.1: O3 / CH2Cl2 / -78 °C 5.2: 64 percent / Me2S / CH2Cl2 / 4 h / 25 °C View Scheme

1.1: 82 percent / aq. NaOH / methanol / Heating 2.1: 92 percent / Me3SiCl / 20 °C 3.1: O3 / CH2Cl2 / -78 °C 3.2: 64 percent / Me2S / CH2Cl2 / 4 h / 25 °C View Scheme

1.1: 90 percent / dimethylsulfoxide 2.1: 82 percent / aq. NaOH / methanol / Heating 3.1: 92 percent / Me3SiCl / 20 °C 4.1: O3 / CH2Cl2 / -78 °C 4.2: 64 percent / Me2S / CH2Cl2 / 4 h / 25 °C View Scheme

1.1: 74 percent / CuCl / tetrahydrofuran / -78 - 25 °C 2.1: 94 percent / LiAlH4 / diethyl ether / Heating 3.1: 88 percent / KOH / tetrahydrofuran / 18 h / 0 °C 4.1: 90 percent / dimethylsulfoxide 5.1: 82 percent / aq. NaOH / methanol / Heating 6.1: 92 percent / Me3SiCl / 20 °C 7.1: O3 / CH2Cl2 / -78 °C 7.2: 64 percent / Me2S / CH2Cl2 / 4 h / 25 °C View Scheme

1.1: 94 percent / LiAlH4 / diethyl ether / Heating 2.1: 88 percent / KOH / tetrahydrofuran / 18 h / 0 °C 3.1: 90 percent / dimethylsulfoxide 4.1: 82 percent / aq. NaOH / methanol / Heating 5.1: 92 percent / Me3SiCl / 20 °C 6.1: O3 / CH2Cl2 / -78 °C 6.2: 64 percent / Me2S / CH2Cl2 / 4 h / 25 °C View Scheme

1.1: 92 percent / Me3SiCl / 20 °C 2.1: O3 / CH2Cl2 / -78 °C 2.2: 64 percent / Me2S / CH2Cl2 / 4 h / 25 °C View Scheme

1.1: 95 percent / aq. NaOH / methanol / Heating 2.1: 92 percent / Me3SiCl / 20 °C 3.1: O3 / CH2Cl2 / -78 °C 3.2: 75 percent / Me2S / CH2Cl2 / 25 °C View Scheme

1.1: 92 percent / Me3SiCl / 20 °C 2.1: O3 / CH2Cl2 / -78 °C 2.2: 75 percent / Me2S / CH2Cl2 / 25 °C View Scheme