4-(N,N-dimethlyamino)pyridine; triethylamine in dichloromethane T=20°C; 2 h;

1: 53 percent / BH3*Me2S / tetrahydrofuran / -20 - 20 °C 2: 94 percent / imidazole / dimethylformamide / 1 h / 20 °C View Scheme

sodium hydroxide; dihydrogen peroxide in methanol 2 h;

1: 93 percent / NaNO2; HCl / H2O / -5 - 20 °C 2: 53 percent / BH3*Me2S / tetrahydrofuran / -20 - 20 °C 3: 94 percent / imidazole / dimethylformamide / 1 h / 20 °C View Scheme

1: 48 percent / 168 h / 28 °C / lipase PS 2: 94 percent / PCC / CH2Cl2 / 3 h 3: 66 percent / 10 N aq. NaOH, 30percent aq. H2O2 / methanol / 2 h View Scheme

1: 80 percent / imidazole / dimethylformamide / 10 h / Ambient temperature 2: 48 percent / 168 h / 28 °C / lipase PS 3: 94 percent / PCC / CH2Cl2 / 3 h 4: 66 percent / 10 N aq. NaOH, 30percent aq. H2O2 / methanol / 2 h View Scheme

1: 94 percent / PCC / CH2Cl2 / 3 h 2: 66 percent / 10 N aq. NaOH, 30percent aq. H2O2 / methanol / 2 h View Scheme

1.1: 1,1,1,3,3,3-hexamethyl-disilazane; n-butyllithium / tetrahydrofuran; hexane / 0.08 h / -80 °C / |Inert atmosphere 1.2: -80 h / |Inert atmosphere 2.1: lithium borohydride; methanol / diethyl ether / 1.5 h / 0 - 20 °C / |Inert atmosphere 3.1: 2,4,6-trimethyl-pyridine / dichloromethane / 3.5 h / -20 °C / |Inert atmosphere 4.1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran; toluene / 22 h / 0 - 20 °C 5.1: selenium(IV) oxide; tert.-butylhydroperoxide / 1,2-dichloro-ethane / 3 h / 60 °C 6.1: triethylamine / dichloromethane / 0 - 20 °C / |Inert atmosphere 7.1: trifluoroacetic acid / dichloromethane / 3 h / -20 °C 8.1: sodium hydride / N,N-dimethyl-formamide / 2 h / 0 - 20 °C / |Inert atmosphere 9.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 h / 20 °C / |Inert atmosphere 10.1: potassium carbonate; methanol / 3 h / 20 °C / |Inert atmosphere 11.1: Dess-Martin periodane / dichloromethane / 2 h / 20 °C / |Inert atmosphere 12.1: 2-methyl-but-2-ene; sodium dihydrogen phosphate dihydrate; sodium chlorite / water; dichloromethane; tert-butyl alcohol / 18 h / 0 °C 13.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / 2 h / 20 °C / |Inert atmosphere 14.1: magnesium; methanol / 3 h / -20 °C / |Inert atmosphere 15.1: caesium carbonate / acetone / 13 h / 0 °C / |Inert atmosphere; |Darkness 16.1: triethylamine; tetrakis(triphenylphosphine) palladium(0); copper(II) sulfate; sodium L-ascorbate / N,N-dimethyl-formamide / 4 h / 80 °C / |Inert atmosphere; |Darkness 17.1: trifluoroacetic acid / dichloromethane / 2 h / 0 °C 18.1: C21H27AuNP(1+)*F6Sb(1-) / 1,2-dichloro-ethane / 1 h / 45 °C / |Inert atmosphere 18.2: 0.42 h / 0 °C / |Inert atmosphere 19.1: acetic acid / toluene / 4 h / 80 °C / |Inert atmosphere 20.1: boron trifluoride diethyl etherate; tetrachlorosilane / 1,2-dichloro-ethane / 12 h / 20 °C / |Inert atmosphere 20.2: 10 h / 60 °C / |Inert atmosphere 21.1: caesium carbonate / acetone / 3.5 h / 20 °C / |Inert atmosphere 22.1: silver nitrate; water; triethylamine / acetone / 16 h / 50 °C 23.1: water; lithium hydroxide hydrate / tetrahydrofuran / 20 °C 23.2: -78 - -30 °C View Scheme

1: 1.) LiHMDS, 2.) TMSCl / 1.) THF, -78 deg C, 1 h, 2.) THF, -78 deg C, 1 h; room temperature, 2 h, 3.) -78 deg C, 3 h; -78 deg C to room temperature, 30 min 2: 98 percent / DIBAL-H / toluene / 1.5 h / -78 °C 3: 98 percent / Et3N, DMAP / CH2Cl2 / 1.) 0 deg C, 1 h, 2.) room temperature, 12 h 4: 100 percent / TMSOTf / 1,2-dichloro-ethane / 1.) 0 deg C, 30 min, 2.) room temperature, 90 min 5: 100 percent / AIBN, Bu3SnH / benzene / 1.5 h / Heating 6: 78 percent / triethylamine trihydrofluoride / tetrahydrofuran / Ambient temperature View Scheme