amberlyst-15 in water; acetone Heating;

1: 54 percent / Al2O3 / 1.) 0 deg C, 70 min; 2.) RT; 3.) CH2Cl2, 50 deg C 2: 48 percent / aq. NaOAc, sodium hypophosphite / Raney-nickel / ethanol; acetic acid / 3 h / 50 °C / pH=5.0 3: 90 percent / Amberlyst-15 / acetone; H2O / Heating View Scheme

1: 77 percent / p-TsOH / benzene / 24 h / Heating; Dean-Stark trap 2: 54 percent / Al2O3 / 1.) 0 deg C, 70 min; 2.) RT; 3.) CH2Cl2, 50 deg C 3: 48 percent / aq. NaOAc, sodium hypophosphite / Raney-nickel / ethanol; acetic acid / 3 h / 50 °C / pH=5.0 4: 90 percent / Amberlyst-15 / acetone; H2O / Heating View Scheme

1: 54 percent / Al2O3 / 1.) 0 deg C, 70 min; 2.) RT; 3.) CH2Cl2, 50 deg C 2: 48 percent / aq. NaOAc, sodium hypophosphite / Raney-nickel / ethanol; acetic acid / 3 h / 50 °C / pH=5.0 3: 90 percent / Amberlyst-15 / acetone; H2O / Heating View Scheme

1: 48 percent / aq. NaOAc, sodium hypophosphite / Raney-nickel / ethanol; acetic acid / 3 h / 50 °C / pH=5.0 2: 90 percent / Amberlyst-15 / acetone; H2O / Heating View Scheme

1: 1.) lithium diisopropylamide / 1.) THF, 5 deg C, 15 min, 2.) room temp., 2 h 2: 91 percent / diethyl ether / 4 h / Ambient temperature 3: 92 percent / sodium borohydride / ethanol / Ambient temperature 4: 80 percent / iodine / acetic acid / 3 h / Heating 5: 1.) ozone, 2.) water / 1.) dichloromethane, methanol, -25 deg C View Scheme

1: 80 percent / iodine / acetic acid / 3 h / Heating 2: 1.) ozone, 2.) water / 1.) dichloromethane, methanol, -25 deg C View Scheme

1: 92 percent / sodium borohydride / ethanol / Ambient temperature 2: 80 percent / iodine / acetic acid / 3 h / Heating 3: 1.) ozone, 2.) water / 1.) dichloromethane, methanol, -25 deg C View Scheme

1: 91 percent / diethyl ether / 4 h / Ambient temperature 2: 92 percent / sodium borohydride / ethanol / Ambient temperature 3: 80 percent / iodine / acetic acid / 3 h / Heating 4: 1.) ozone, 2.) water / 1.) dichloromethane, methanol, -25 deg C View Scheme

water; ozone 1.) dichloromethane, methanol, -25 deg C; Yield given. Multistep reaction;