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: 1.) n-BuLi; 2.) CuI-Bu3P, and Bu3P / 1.) THF, -78 deg C, 20 min, 30 min; 2.) THF, ether, -78 deg C 10 min, - 30 deg C 1 h; 3.) THF, ether, HMPA, -30 deg C, 3 h 2: 78 percent / pyridine, 50percent aq. HF / 1.) 0 deg C, 30 min; 2.) rt, 4.5 h 3: aluminum amalgam / tetrahydrofuran; H2O / addition in equal portion after 10 h, 17 h and 23h; rt 15 h View Scheme

sodium iodide in acetone 0.0833333 h; with longer reaction time the cis-isomer began to isomerized to trans-isomer;

1: 85 percent / p-toluenesulfonic acid hydrate / 36 h / Heating 2: hydrogen / Lindlar catalyst / hexane; ethyl acetate / 0 °C 3: 96 percent / carbon tetrabromide, triphenylphosphine / CH2Cl2 / 0.67 h 4: 99.9 percent / NaI / acetone / 0.08 h / with longer reaction time the cis-isomer began to isomerized to trans-isomer View Scheme

1: H2 / Lindlar's catalyst / ethyl acetate 2: camphorsulfonic acid / methanol 3: CBr4, triphenylphosphine / acetonitrile 4: NaI / acetone View Scheme

1: camphorsulfonic acid / methanol 2: CBr4, triphenylphosphine / acetonitrile 3: NaI / acetone View Scheme

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;

Yield given. Multistep reaction;