1: 1.) O3, NaHCO3, 2.) Et3N / 1.) CH2Cl2, MeOH, 2.) CH2Cl2, a) 0 deg C, 15 min, b) RT, 4 h 2: 1.) t-BuOK / 1.) THF, DMSO, -10 deg C, 30 min, 2.) THF, -10 deg C 3: H2 / Pd/C / acetone 4: 5percent aq. NaOH / methanol View Scheme

1: 1.) t-BuOK / 1.) THF, DMSO, -10 deg C, 30 min, 2.) THF, -10 deg C 2: H2 / Pd/C / acetone 3: 5percent aq. NaOH / methanol View Scheme

1: 1.) t-BuOK / 1.) THF, DMSO, -10 deg C, 30 min, 2.) THF, -10 deg C 2: H2 / Pd/C / acetone 3: 5percent aq. NaOH / methanol View Scheme

potassium hydroxide in methanol 70 h; heating, sealed tube;

sodium hydroxide in methanol

1: 1.) Et3N / 1.) CH2Cl2, 0 deg C, 15 min, 2.) CH2Cl2, 30 min 2: CH2Cl2 / 1 h View Scheme