sodium periodate; ruthenium trichloride in water; ethyl acetate; acetonitrile 0.5 h;

1: liq. NH3 2: P2O5 / benzene / Heating 3: KMnO4, aq. KOH View Scheme

1: P2O5 / benzene / Heating 2: KMnO4, aq. KOH View Scheme

potassium hydroxide; potassium permanganate

(i) O3, (ii) (hydrolysis); Multistep reaction;

1: caesium carbonate / N,N-dimethyl-formamide / 3 h / 20 °C / |Inert atmosphere 2: palladium 10 on activated carbon; hydrogen / methanol / 0.33 h View Scheme

1.1: sulfuric acid / 16 h / 7 - 12 °C / Reflux 2.1: N,N,N',N',N'',N''-hexamethylphosphoric triamide; diisopropylamine; n-butyllithium / tetrahydrofuran; hexanes / 2 h / -73 - -10 °C / Inert atmosphere 2.2: 16 h / -70 - 20 °C 3.1: sodium hydroxide; water / tetrahydrofuran; methanol / 16 h / 15 - 20 °C 3.2: 10 °C / pH ~ 4 4.1: N-ethyl-N,N-diisopropylamine; diphenyl phosphoryl azide / toluene / 2 h / 10 - 110 °C 4.2: 40 h / 110 °C 5.1: hydrogenchloride; hydrogen / palladium 10 on activated carbon / methanol / 10 h / 1551.49 Torr View Scheme