1: n-BuLi / tetrahydrofuran / -78 °C 2: 1.) copper(I) iodide, tributylphosphine; 2.) HMPA / 1.) THF, -78 deg C; 2.) -30 deg C, 3 h 3: 89 percent / aqu. HF, pyridine / acetonitrile 4: 98 percent / Al(Hg) / tetrahydrofuran; H2O 5: enzyme View Scheme

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: zinc; titanium tetrachloride / tetrahydrofuran; dichloromethane / 1.5 h / 25 °C / |Cooling with ice 3.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 0 °C / |Inert atmosphere 3.2: 1.75 h / 0 - 20 °C 4.1: triethylamine / dichloromethane / 0 °C / |Inert atmosphere 5.1: hydrogen; potassium hydroxide; 5 palladium on charcoal / methanol / 5 h 6.1: sodium hydride / tetrahydrofuran; mineral oil / 4 h / 0 °C / |Inert atmosphere; |Reflux 7.1: acetic acid / tetrahydrofuran; water / 20 °C 8.1: hydrogen; potassium hydroxide; 5 palladium on charcoal / methanol / 20 °C 9.1: potassium carbonate; tetrabutylammomium bromide / acetone / 30 °C 10.1: water; potassium hydroxide / methanol / 3 h / |Reflux 10.2: pH 2 View Scheme

1: n-BuLi / tetrahydrofuran / -78 °C 2: 1.) copper(I) iodide, tributylphosphine; 2.) HMPA / 1.) THF, -78 deg C; 2.) -30 deg C, 3 h 3: 89 percent / aqu. HF, pyridine / acetonitrile 4: 98 percent / Al(Hg) / tetrahydrofuran; H2O View Scheme

Yield given. Multistep reaction;