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

1: 95 percent / tetrahydrofuran / 0.25 h / -78 °C / -50 deg C, 10 min 2: 80 percent / tetrabutylammonium fluoride / tetrahydrofuran / 24 h / 25 °C 3: 88 percent / lithium, liquid NH3 / 2-methyl-propan-2-ol; tetrahydrofuran / 0.25 h / -78 °C 4: 57 percent / O2, sodium bicarbonate / Pt / acetone; H2O / 2 h / 57 °C View Scheme

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

Yield given. Multistep reaction. Yields of byproduct given;

1.) THF, -78 deg C, 2.) -40 deg C -> 0 deg C, 1 h; Yield given. Multistep reaction. Yields of byproduct given;

Yield given. Multistep reaction. Yields of byproduct given;

Yield given. Multistep reaction. Yields of byproduct given;

Yield given. Multistep reaction. Yields of byproduct given;