1: lead tetraacetate (LTA) / tetrahydrofuran / 0 °C 2: NaBH4 / methanol / 0 °C 3: Et3N 4: NaN3 / dimethylsulfoxide / 80 °C View Scheme

1: 2N HCl / Ambient temperature 2: lead tetraacetate (LTA) / tetrahydrofuran / 0 °C 3: NaBH4 / methanol / 0 °C 4: Et3N 5: NaN3 / dimethylsulfoxide / 80 °C View Scheme

1: MgI2 etherate / neat (no solvent) / 20 - 65 °C 2: sodium azide / N,N-dimethyl-formamide / 12 h / 85 °C View Scheme

1.1: Inert atmosphere 2.1: [Ni0(1,5-cyclooctadiene)2]; sodium t-butanolate; 1,3-bis(2,6-diisopropylphenyl)imidazolinium chloride / 1,4-dioxane / 3 h / 80 °C / Inert atmosphere 3.1: N-iodo-succinimide; trifluoroacetic acid / 14 h / 23 °C / Inert atmosphere 3.2: 23 °C 4.1: trans-1,2-cyclohexanediamine; potassium carbonate; copper(l) chloride / 1,4-dioxane / 15 h / 110 °C / Inert atmosphere; Darkness View Scheme

1.1: Inert atmosphere 2.1: Inert atmosphere 3.1: [Ni0(1,5-cyclooctadiene)2]; sodium t-butanolate; 1,3-bis(2,6-diisopropylphenyl)imidazolinium chloride / 1,4-dioxane / 3 h / 80 °C / Inert atmosphere 4.1: N-iodo-succinimide; trifluoroacetic acid / 14 h / 23 °C / Inert atmosphere 4.2: 23 °C 5.1: trans-1,2-cyclohexanediamine; potassium carbonate; copper(l) chloride / 1,4-dioxane / 15 h / 110 °C / Inert atmosphere; Darkness View Scheme

1.1: n-butyllithium / hexane; tetrahydrofuran / 3.5 h / -78 °C / Inert atmosphere 1.2: -78 - 20 °C 1.3: 0.5 h / 20 °C 2.1: triethylamine / dichloromethane / 18 h / 0 - 20 °C 3.1: sodium azide / N,N-dimethyl-formamide / 4 h / 80 - 85 °C View Scheme

water; triphenylphosphine in tetrahydrofuran T=70°C;

10 palladium on activated charcoal; hydrogen in methanol T=20°C; P=1034.32 Torr; 3 h;

1: T=23°C; 7 h; 2: With potassium hydroxide in water T=23°C;

1: hydrogen / Pd/C / ethyl acetate / 12 h / 760 Torr 2: pyridine View Scheme