dihydrogen peroxide in tetrahydrofuran T=0°C; 0.5 h; Yields of byproduct given;

1: 1.) Br2; 2.) LiBr/Li2CO3 / 1.) CHCl3, RT, 1 h; 2.) DMF, 125-130 deg C, 45 min 2: 37 percent / CrO3/tert-BuOH/Ac2O / CCl4 / 72 h / Heating 3: 1.) H2; 2.) NaBH4 / 1.) RhCl(PPh3)3 / 1.) benzene/EtOH, 2-3 d; 2.) MeOH, -20 - -18 deg C, 30 min 4: 11.4 mg / 1.) 3 N NaOH; 2.) 3 N HCl / tetrahydrofuran / 1.) RT, 30 min; 2.) 1 h 5: 73 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone(DDQ) / dioxane / 27 h / Heating 6: 19 percent / 1.) lithium diisopropylamide (LDA); 2.) hexamethylphosphoramide (HMPA) / tetrahydrofuran / -78 °C / 1.) 30 min; 2.) 3 h 7: 37 percent / 35percent H2O2 / tetrahydrofuran / 0.5 h / 0 °C View Scheme

1: 78 percent / p-TsOH / 72 h / Heating 2: 1,8-diazabicyclo<5.4.0>undec-7-ene / benzene / 1.5 h / 80 °C 3: 37 percent / CrO3/tert-BuOH/Ac2O / CCl4 / 72 h / Heating 4: 1.) H2; 2.) NaBH4 / 1.) RhCl(PPh3)3 / 1.) benzene/EtOH, 2-3 d; 2.) MeOH, -20 - -18 deg C, 30 min 5: 11.4 mg / 1.) 3 N NaOH; 2.) 3 N HCl / tetrahydrofuran / 1.) RT, 30 min; 2.) 1 h 6: 73 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone(DDQ) / dioxane / 27 h / Heating 7: 19 percent / 1.) lithium diisopropylamide (LDA); 2.) hexamethylphosphoramide (HMPA) / tetrahydrofuran / -78 °C / 1.) 30 min; 2.) 3 h 8: 37 percent / 35percent H2O2 / tetrahydrofuran / 0.5 h / 0 °C View Scheme

1: diethyl ether / Ambient temperature 2: 95 percent / CrO3, pyridine / CH2Cl2 / 6 h / 0 °C 3: 84 percent / LiAlH(OtBu)3 / tetrahydrofuran / 3 h / 0 °C 4: 99 percent / CSA / benzene / 0.5 h / Heating 5: 49 percent / LDA, HMPA / hexane; tetrahydrofuran / -78 - -40 °C 6: 33 percent / 30percent H2O2, acetic acid / H2O; tetrahydrofuran View Scheme

1: Zn dust, acetic acid / methanol / 0.25 h / Heating 2: diethyl ether / Ambient temperature 3: 95 percent / CrO3, pyridine / CH2Cl2 / 6 h / 0 °C 4: 84 percent / LiAlH(OtBu)3 / tetrahydrofuran / 3 h / 0 °C 5: 99 percent / CSA / benzene / 0.5 h / Heating 6: 49 percent / LDA, HMPA / hexane; tetrahydrofuran / -78 - -40 °C 7: 33 percent / 30percent H2O2, acetic acid / H2O; tetrahydrofuran View Scheme

1: 56 percent / 5percent HCl / dimethylformamide / 4 h / 90 °C 2: Zn dust, acetic acid / methanol / 0.25 h / Heating 3: diethyl ether / Ambient temperature 4: 95 percent / CrO3, pyridine / CH2Cl2 / 6 h / 0 °C 5: 84 percent / LiAlH(OtBu)3 / tetrahydrofuran / 3 h / 0 °C 6: 99 percent / CSA / benzene / 0.5 h / Heating 7: 49 percent / LDA, HMPA / hexane; tetrahydrofuran / -78 - -40 °C 8: 33 percent / 30percent H2O2, acetic acid / H2O; tetrahydrofuran View Scheme