1: 83 percent / POCl3, pyridine / 17 h / 85 °C 2: 1) BH3*THF, 2) 3 M NaOH, 30percent H2O2 / 1) THF, 0 deg C, 20 h, 2) THF, r.t., 3 h 3: 1) (COCl)2, DMSO, 2) Et3N / 1) CH2Cl2, -78 deg C, 2 min, 2) CH2Cl2, -78 deg C, 1 h 4: 1 M KMnO4 / 2-methyl-propan-2-ol / 0.08 h / pH 7 phosphate buffer 5: 86 percent / 1 M NaOH, Na2RuO4 / 0.5 h / Ambient temperature 6: Ac2O / CH2Cl2 / 3.5 h / Heating 7: 1) Bu2SnO / 1) benzene, reflux, 24 h, 2) toluene, a) -40 deg C, 2 h, b) to r.t. 8: 1) Et3N, 2,4,6-trichlorobenzoyl chloride, 2) 4-(dimethylamino)pyridine / 1) THF, r.t., 3.5 h, 2) THF, toluene, reflux, 10 min 9: 86 percent / Ph3C*BF4 / CH2Cl2 / 48 h / Heating View Scheme

1: 1) (COCl)2, DMSO, 2) Et3N / 1) CH2Cl2, -78 deg C, 2 min, 2) CH2Cl2, -78 deg C, 1 h 2: 1 M KMnO4 / 2-methyl-propan-2-ol / 0.08 h / pH 7 phosphate buffer 3: 86 percent / 1 M NaOH, Na2RuO4 / 0.5 h / Ambient temperature 4: Ac2O / CH2Cl2 / 3.5 h / Heating 5: 1) Bu2SnO / 1) benzene, reflux, 24 h, 2) toluene, a) -40 deg C, 2 h, b) to r.t. 6: 1) Et3N, 2,4,6-trichlorobenzoyl chloride, 2) 4-(dimethylamino)pyridine / 1) THF, r.t., 3.5 h, 2) THF, toluene, reflux, 10 min 7: 86 percent / Ph3C*BF4 / CH2Cl2 / 48 h / Heating View Scheme

1: 1) Et3N, 2,4,6-trichlorobenzoyl chloride, 2) 4-(dimethylamino)pyridine / 1) THF, r.t., 3.5 h, 2) THF, toluene, reflux, 10 min 2: 86 percent / Ph3C*BF4 / CH2Cl2 / 48 h / Heating View Scheme

hydrogenchloride

1: 81 percent / Ba(OH)2*8H2O / 2 h / heating 2: 40 percent / o-bromanil / CHCl3 / 0.03 h View Scheme

acetyl chloride

1: With chloranil in chloroform T=20°C; 2: With sodium tetrahydroborate; potassium hydroxide in chloroform

1: Ba(OH)2; water 2: KOBr View Scheme

ethanol; dihydrogen peroxide

acetyl chloride