1.1: n-butyllithium; copper (I) cyanide; methyllithium / diethyl ether; hexane; tetrahydrofuran / 0.5 h / -70 °C 1.2: 0.5 h / -70 °C 2.1: toluene-4-sulfonic acid / tetrahydrofuran; dichloromethane / 1.5 h / 25 °C / |Cooling with ice 2.2: 1 h / 20 °C 3.1: 1H-imidazole / ethyl acetate / 20 °C 4.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 0 °C / |Inert atmosphere 4.2: 1.75 h / 0 - 20 °C 5.1: triethylamine / dichloromethane / 0 °C / |Inert atmosphere 6.1: hydrogen; potassium hydroxide; 5 palladium on charcoal / methanol / 5 h 7.1: sodium hydride / tetrahydrofuran; mineral oil / 4 h / 0 °C / |Inert atmosphere; |Reflux 8.1: acetic acid / tetrahydrofuran; water / 20 °C 9.1: hydrogen; potassium hydroxide; 5 palladium on charcoal / methanol / 20 °C 10.1: potassium carbonate; tetrabutylammomium bromide / acetone / 30 °C 11.1: water; potassium hydroxide / methanol / 3 h / |Reflux 11.2: pH 2 View Scheme

1: 51 percent / Mo[N(t-Bu)(3,5-diMePh)]3/CH2Cl2 / toluene; CH2Cl2 / 9 h / 80 °C 2: 87 percent / H2; quinoline / Lindlar catalyst / hexane / 760.05 Torr 3: 88 percent / aq. HF / tetrahydrofuran / 1 h View Scheme

1: 0.2368 g / aq. AcOH / tetrahydrofuran / 9 h / 20 °C 2: 96 percent / diisopropyl carbodiimide; DMAP / CH2Cl2 / 3 h / 20 °C 3: 77 percent / CH2Cl2 / Mo[N(t-Bu)(p-PhF)]3/CH2Cl2 / toluene / 16 h / 80 °C 4: 86 percent / H2; quinoline / Lindlar catalyst / hexane / 2 h / 760.05 Torr 5: 88 percent / aq. HF / acetonitrile / 1 h View Scheme