triethylamine in dichloromethane T=0 - 5°C; 1-2 h;

triethylamine in toluene

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 5: 88 percent / triethylamine / CH2Cl2 / 0 - 5 °C / 1-2 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 4: 88 percent / triethylamine / CH2Cl2 / 0 - 5 °C / 1-2 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 5: 88 percent / triethylamine / CH2Cl2 / 0 - 5 °C / 1-2 h View Scheme

1: 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 2: 1.) ozone, Sudan red, 2.) NaBH4, NaOH / 1.) CH2Cl2, ethanol, 2.) CH2Cl2, ethanol, 25 deg C, 12-16 h 3: 88 percent / triethylamine / CH2Cl2 / 0 - 5 °C / 1-2 h View Scheme

1: 1.) ozone, Sudan red, 2.) NaBH4, NaOH / 1.) CH2Cl2, ethanol, 2.) CH2Cl2, ethanol, 25 deg C, 12-16 h 2: 88 percent / triethylamine / CH2Cl2 / 0 - 5 °C / 1-2 h View Scheme

1.1: B. lentus protease aqueous formulations / 8 h / 20 °C / pH 7 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 3.33 h / 0 - 12 °C / |Inert atmosphere 3.1: 4-(N,N-dimethlyamino)pyridine / pyridine / 5 - 50 °C 4.1: ozone / dichloromethane; methanol / -50 - -25 °C 4.2: -5 - 20 °C 5.1: triethylamine / dichloromethane / 2.33 h / 0 - 5 °C View Scheme