1: 96.4 percent / 4-(dimethylamino)pyridine / CH2Cl2; pyridine / 1.) 0 deg C,; 2.) room temperature 13 h 2: 89.5 percent / osmium tetraoxide, trimethylamine N-oxide dihydrate / tetrahydrofuran; acetone; H2O / 15 h / Ambient temperature 3: 99 percent / p-toluenesulfonic acid hydrate / 60 h 4: 99 percent / KOH / methanol / 0.5 h 5: 88 percent / trifluoroacetic acid, 1,3-dicyclohexylcarbodiimide / benzene; pyridine; dimethylsulfoxide / 18 h 6: 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 7: 78 percent / pyridine, 50percent aq. HF / 1.) 0 deg C, 30 min; 2.) rt, 4.5 h 8: aluminum amalgam / tetrahydrofuran; H2O / addition in equal portion after 10 h, 17 h and 23h; rt 15 h View Scheme

1: 99 percent / p-toluenesulfonic acid hydrate / 60 h 2: 99 percent / KOH / methanol / 0.5 h 3: 88 percent / trifluoroacetic acid, 1,3-dicyclohexylcarbodiimide / benzene; pyridine; dimethylsulfoxide / 18 h 4: 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 5: 78 percent / pyridine, 50percent aq. HF / 1.) 0 deg C, 30 min; 2.) rt, 4.5 h 6: aluminum amalgam / tetrahydrofuran; H2O / addition in equal portion after 10 h, 17 h and 23h; rt 15 h View Scheme

1: 88 percent / trifluoroacetic acid, 1,3-dicyclohexylcarbodiimide / benzene; pyridine; dimethylsulfoxide / 18 h 2: 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 3: 78 percent / pyridine, 50percent aq. HF / 1.) 0 deg C, 30 min; 2.) rt, 4.5 h 4: aluminum amalgam / tetrahydrofuran; H2O / addition in equal portion after 10 h, 17 h and 23h; rt 15 h View Scheme

1: 99.9 percent / NaI / acetone / 0.08 h / with longer reaction time the cis-isomer began to isomerized to trans-isomer 2: 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 3: 78 percent / pyridine, 50percent aq. HF / 1.) 0 deg C, 30 min; 2.) rt, 4.5 h 4: aluminum amalgam / tetrahydrofuran; H2O / addition in equal portion after 10 h, 17 h and 23h; rt 15 h 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

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

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

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

1: 95 percent / CrO3, H2SO4 / acetone 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

1: 8 percent / 30percent H2O2, Potassium carbonate / methanol; acetonitrile; H2O / 5 h / 0 °C 2: 82 percent / NaBH4, NaOMe / methanol / 0.5 h 3: 83 percent / paraformaldehyde, BF3*Et2O / acetone; H2O / 120 h / Ambient temperature View Scheme