Pd-C in ethyl acetate

1: With ozone in methanol; dichloromethane T=-50 - -25°C; 2: With sodium tetrahydroborate in methanol; dichloromethane; water T=-5 - 20°C; Temperature;

1: With ozone in methanol; dichloromethane T=-78°C; ozonolysis; 2: With sodium hydroxide; sodium tetrahydroborate reductive hydrolysis;

N2; ozone; sodium borohydride; ammonium chloride in ethanol; water

1: triethylamine / CH2Cl2 / 24 h / 20 - 25 °C 2: 1.) CuI / 1.) THF, -30 deg C, 15 min, 2.) THF, -30 deg C, 1 h 3: 1.) potassium tert-butoxide / 1.) THF, 45 deg C, 45 min; other reagents: NaH, NaOH/tetrabutylammonium bromide, NaOH/tetrabutylammonium fluoride, 2.) THF, 21 deg C, 1 h 4: 1.) ozone, Sudan red, 2.) NaBH4, NaOH / 1.) CH2Cl2, ethanol, 2.) CH2Cl2, ethanol, 25 deg C, 12-16 h View Scheme

1: 1.) CuI / 1.) THF, -30 deg C, 15 min, 2.) THF, -30 deg C, 1 h 2: 1.) potassium tert-butoxide / 1.) THF, 45 deg C, 45 min; other reagents: NaH, NaOH/tetrabutylammonium bromide, NaOH/tetrabutylammonium fluoride, 2.) THF, 21 deg C, 1 h 3: 1.) ozone, Sudan red, 2.) NaBH4, NaOH / 1.) CH2Cl2, ethanol, 2.) CH2Cl2, ethanol, 25 deg C, 12-16 h View Scheme

1: 1.48 kg / KOH / ethanol / room temperature -> 0 deg C 2: 1.) CuI / 1.) THF, -30 deg C, 15 min, 2.) THF, -30 deg C, 1 h 3: 1.) potassium tert-butoxide / 1.) THF, 45 deg C, 45 min; other reagents: NaH, NaOH/tetrabutylammonium bromide, NaOH/tetrabutylammonium fluoride, 2.) THF, 21 deg C, 1 h 4: 1.) ozone, Sudan red, 2.) NaBH4, NaOH / 1.) CH2Cl2, ethanol, 2.) CH2Cl2, ethanol, 25 deg C, 12-16 h View Scheme

1.1: 98 percent / t-BuOK / tetrahydrofuran 2.1: O3 / CH2Cl2; methanol / -78 °C 2.2: 83 percent / NaBH4, aq. NaOH View Scheme

1.1: 90 percent / OsO4, NaIO4 / diethyl ether; H2O 2.1: diethyl ether / 4 h / -78 °C 2.2: 91 percent / water / 12 h 3.1: 98 percent / t-BuOK / tetrahydrofuran 4.1: O3 / CH2Cl2; methanol / -78 °C 4.2: 83 percent / NaBH4, aq. NaOH View Scheme

1.1: diethyl ether / 4 h / -78 °C 1.2: 91 percent / water / 12 h 2.1: 98 percent / t-BuOK / tetrahydrofuran 3.1: O3 / CH2Cl2; methanol / -78 °C 3.2: 83 percent / NaBH4, aq. NaOH View Scheme