Burgess Reagent in benzene T=50°C; 2 h;

lead(IV) acetate in acetic acid T=25°C; 2 h;

1: 70 percent / Et2AlCl / CH2Cl2 / 0.25 h / Ambient temperature 2: 93 percent / DIBALH / toluene / 0.33 h / -78 °C 3: 83 percent / imidazole / dimethylformamide 4: 1.) O3, 2.) Ph3P / 1) CH2Cl2, MeOH, -78 deg C; 2) CH2Cl2, MeOH, rt 5: 95 percent / KOH / methanol / 20 h / 60 °C 6: 100 percent / HF / acetonitrile / 2 h 7: 72 percent / Dess-Martin periodinane / CH2Cl2 View Scheme

1: 93 percent / DIBALH / toluene / 0.33 h / -78 °C 2: 83 percent / imidazole / dimethylformamide 3: 1.) O3, 2.) Ph3P / 1) CH2Cl2, MeOH, -78 deg C; 2) CH2Cl2, MeOH, rt 4: 95 percent / KOH / methanol / 20 h / 60 °C 5: 100 percent / HF / acetonitrile / 2 h 6: 72 percent / Dess-Martin periodinane / CH2Cl2 View Scheme

1: 91 percent / NaIO4 / ethanol / 0.25 h 2: 80 percent / MeOOCN(1-)SO2N(1+)Et3 / benzene / 2 h / 50 °C View Scheme

1: 2.) 6N HCl / 1.) ether, THF, -79 deg C, 1 h; 2.) MeOH, -30 deg C, 3 h 2: 91 percent / NaIO4 / ethanol / 0.25 h 3: 80 percent / MeOOCN(1-)SO2N(1+)Et3 / benzene / 2 h / 50 °C View Scheme

Multistep reaction;