sulfuric acid 2 h; Heating;

1: (acid hydrolysis) 3: NaOMe, Br2 4: (i) HNO2, (ii) CrO3 5: HCl / dioxane View Scheme

1: 62.5 percent / Red-Al / tetrahydrofuran / 3 h 2: 79.7 percent / aq. HBr; Ac2O / 5 h / Heating View Scheme

sodium bis(2-methoxyethoxy)aluminium dihydride in tetrahydrofuran 3 h;

1: lithium aluminium tetrahydride / tetrahydrofuran 2: 1H-imidazole / N,N-dimethyl-formamide 3: 1H-imidazole; iodine; triphenylphosphine / toluene 4: n-butyllithium; N,N,N',N',N'',N''-hexamethylphosphoric triamide / tetrahydrofuran 5: hydrogen; palladium on activated charcoal / ethyl acetate 6: pyridinium chlorochromate / dichloromethane 7: sodium hexamethyldisilazane / tetrahydrofuran 8: tetrabutyl ammonium fluoride / tetrahydrofuran 9: hydrogen; palladium 10 on activated carbon / ethyl acetate View Scheme