1.1: lithium tri-t-butoxyaluminum hydride / ethanol / 2 h / -78 °C / Inert atmosphere 2.1: Grubb's 2nd generation catalyst / dichloromethane / 24 h / Inert atmosphere; Reflux 3.1: palladium 10 on activated carbon; hydrogen / ethyl acetate / 25 °C 4.1: pyridine / dichloromethane / 4 h / 25 °C / Inert atmosphere 5.1: toluene-4-sulfonic acid / methanol / 2 h / 25 °C / Inert atmosphere 5.2: 2 h / 25 °C / Inert atmosphere View Scheme

1.1: Grubb's 2nd generation catalyst / dichloromethane / 24 h / Inert atmosphere; Reflux 2.1: palladium 10 on activated carbon; hydrogen / ethyl acetate / 25 °C 3.1: pyridine / dichloromethane / 4 h / 25 °C / Inert atmosphere 4.1: toluene-4-sulfonic acid / methanol / 2 h / 25 °C / Inert atmosphere 4.2: 2 h / 25 °C / Inert atmosphere View Scheme

1.1: palladium 10 on activated carbon; hydrogen / ethyl acetate / 25 °C 2.1: pyridine / dichloromethane / 4 h / 25 °C / Inert atmosphere 3.1: toluene-4-sulfonic acid / methanol / 2 h / 25 °C / Inert atmosphere 3.2: 2 h / 25 °C / Inert atmosphere View Scheme

1.1: 1H-imidazole; iodine; triphenylphosphine / toluene 2.1: zinc / tetrahydrofuran; water 3.1: lithium tri-t-butoxyaluminum hydride / ethanol / 2 h / -78 °C / Inert atmosphere 4.1: Grubb's 2nd generation catalyst / dichloromethane / 24 h / Inert atmosphere; Reflux 5.1: palladium 10 on activated carbon; hydrogen / ethyl acetate / 25 °C 6.1: pyridine / dichloromethane / 4 h / 25 °C / Inert atmosphere 7.1: toluene-4-sulfonic acid / methanol / 2 h / 25 °C / Inert atmosphere 7.2: 2 h / 25 °C / Inert atmosphere View Scheme

1.1: zinc / tetrahydrofuran; water 2.1: lithium tri-t-butoxyaluminum hydride / ethanol / 2 h / -78 °C / Inert atmosphere 3.1: Grubb's 2nd generation catalyst / dichloromethane / 24 h / Inert atmosphere; Reflux 4.1: palladium 10 on activated carbon; hydrogen / ethyl acetate / 25 °C 5.1: pyridine / dichloromethane / 4 h / 25 °C / Inert atmosphere 6.1: toluene-4-sulfonic acid / methanol / 2 h / 25 °C / Inert atmosphere 6.2: 2 h / 25 °C / Inert atmosphere View Scheme

1: pyridine 2: diethylazodicarboxylate; triphenylphosphine / tetrahydrofuran / 20 °C 3: sodium methylate / methanol 4: toluene-4-sulfonic acid / methanol; dichloromethane View Scheme

1: sodium methylate / methanol 2: toluene-4-sulfonic acid / methanol; dichloromethane View Scheme

1: 84 percent / tetramethylguanidinium azide / dimethylformamide / 48 h / 20 °C 2: 94 percent / H2 / Pd/C / methanol / 48 h / 20 °C View Scheme