lithium diisopropyl amide in tetrahydrofuran T=0 - 20°C; 10 h;

[2,2']bipyridinyl; n-butyllithium; diisopropylamine 1) THF, 0 deg C, 15 min, 2) 0 deg C, 5 min; Yield given. Multistep reaction;

sodium hydroxide; sodium tetrahydroborate in ethanol T=20°C; 2 h;

1: -78 °C 2: 64 percent / tetrahydrofuran / -78 °C 3: pyridine / 6 h / Ambient temperature 4: water / H2SO4 / methanol / 30 h / Ambient temperature 5: 91 percent / n-butyllithium / tetrahydrofuran / 0 °C 6: water, oxalic acid / methanol / 4 h / Ambient temperature 8: m-chloroperbenzoic acid / CH2Cl2 / 4.5 h / Ambient temperature 9: LiAlH4 / diethyl ether / 1 h / Ambient temperature 10: pyridine / 80 °C 11: 0.5 h / 150 °C View Scheme

1.1: H2O2, NaOH / methanol 2.1: L-selectride / tetrahydrofuran / -65 °C 3.1: imidazole 4.1: OsO4, KIO4 4.2: MCPBA 5.1: K2CO3 / methanol 6.1: imidazole View Scheme

cultured cells of Catharanthus roseus; [14C]-Sucrose in water T=25°C; 24 h; other reaction time; Product distribution;

1.1: methyl lithium LiBr complex / tetrahydrofuran; diethyl ether / 0.45 h / -78 °C / Inert atmosphere 2.1: water; potassium hydroxide / 1,4-dioxane / 6 h / 20 - 75 °C 3.1: 1H-imidazole / N,N-dimethyl-formamide / 24 h / 20 °C / Inert atmosphere 4.1: pyridinium chlorochromate / dichloromethane / 54 h / 23 °C 5.1: iodine; magnesium; mercury dichloride / diethyl ether; toluene / 20 h / 20 °C / Inert atmosphere 6.1: 1H-imidazole / N,N-dimethyl-formamide / 72 h / 20 °C 7.1: platinum (IV)-chloride; isopropyl alcohol; cyclooctadiene / toluene / 0.33 h / 23 °C 8.1: toluene-4-sulfonic acid / tetrahydrofuran / 20 h / 65 °C 9.1: diisobutylaluminium hydride / hexane; dichloromethane / 0.67 h / 0 °C / Inert atmosphere 10.1: tetrabutyl ammonium fluoride / dichloromethane / 40 h / 23 °C 11.1: bis(acetylacetonate)oxovanadium / dichloromethane / 23 °C 11.2: 25 h / 23 °C 12.1: sulfur trioxide pyridine complex; N-ethyl-N,N-diisopropylamine / dichloromethane; dimethyl sulfoxide / 27 h / 23 °C 13.1: potassium tert-butylate / tetrahydrofuran / 0.17 h / -78 °C 13.2: 8 h / -78 - -20 °C 14.1: lithium aluminium tetrahydride / tetrahydrofuran / 24 h / 60 °C / Inert atmosphere 15.1: sulfuric acid; water; mercury(II) oxide / acetone / 20 h / 23 °C View Scheme

0.1 h; microwave irradiation;

hydrogen in dichloromethane T=24.84°C; P=750.075 Torr; 23 h;