1: 99 percent / imidazole, DMAP / dimethylformamide / 0.75 h / 0 °C 2: 85 percent / NCS, AgNO3 / acetonitrile; H2O; CH2Cl2 / 0.12 h / 0 °C 3: 1.) Ph3P / 1.) CH2Cl2, 0 deg C, 1h, 2.) -78 deg C, 40 min 4: 1.) BuLi / 1.) THF, hexane, -78 deg C, 1h, 2.) THF, hexane, HMPA, RT, 30 min 5: 99 percent / H2 / Lindlar catalyst / ethyl acetate / 0.5 h / Ambient temperature 6: 70 percent / Bu4NF / tetrahydrofuran / 1 h / Ambient temperature 7: 1.) DMSO/oxalyl chloride, 2.) NEt3 / 1.) CH2Cl2, -78 deg C, 30 min, 2.) -78 deg C to 0 deg C 8: 70percent ButOOH, 10percent aq. NaOH / tetrahydrofuran / 0.5 h / 0 °C 9: 1.) KOH, 2.) Ph3P, diethyl azodicarboxylate / 1.) MeOH, 60 deg C, 3h, 2.) benzene, RT, 13h View Scheme

1: 98 percent / imidazole, DMAP / dimethylformamide / 0.75 h / 0 °C 2: 85 percent / NCS, AgNO3 / acetonitrile; H2O; CH2Cl2 / 0.12 h / 0 °C 3: 1.) Ph3P / 1.) CH2Cl2, 0 deg C, 1h, 2.) -78 deg C, 40 min 4: 1.) BuLi / 1.) THF, hexane, -78 deg C, 1h, 2.) THF, hexane, HMPA, RT, 30 min 5: 95 percent / H2 / Lindlar catalyst / ethyl acetate / 0.5 h / Ambient temperature 6: 68 percent / Bu4NF / tetrahydrofuran / 1 h / Ambient temperature 7: 1.) DMSO/oxalyl chloride, 2.) NEt3 / 1.) CH2Cl2, -78 deg C, 30 min, 2.) -78 deg C to 0 deg C 8: 70percent ButOOH, 10percent aq. NaOH / tetrahydrofuran / 0.5 h / 0 °C 9: 1.) KOH, 2.) Ph3P, diethyl azodicarboxylate / 1.) MeOH, 60 deg C, 3h, 2.) benzene, RT, 13h View Scheme

1: 1.) BuLi / 1.) THF, hexane, -78 deg C, 1h, 2.) THF, hexane, HMPA, RT, 30 min 2: 99 percent / H2 / Lindlar catalyst / ethyl acetate / 0.5 h / Ambient temperature 3: 70 percent / Bu4NF / tetrahydrofuran / 1 h / Ambient temperature 4: 1.) DMSO/oxalyl chloride, 2.) NEt3 / 1.) CH2Cl2, -78 deg C, 30 min, 2.) -78 deg C to 0 deg C 5: 70percent ButOOH, 10percent aq. NaOH / tetrahydrofuran / 0.5 h / 0 °C 6: 1.) KOH, 2.) Ph3P, diethyl azodicarboxylate / 1.) MeOH, 60 deg C, 3h, 2.) benzene, RT, 13h View Scheme

1: 99 percent / H2 / Lindlar catalyst / ethyl acetate / 0.5 h / Ambient temperature 2: 70 percent / Bu4NF / tetrahydrofuran / 1 h / Ambient temperature 3: 1.) DMSO/oxalyl chloride, 2.) NEt3 / 1.) CH2Cl2, -78 deg C, 30 min, 2.) -78 deg C to 0 deg C 4: 70percent ButOOH, 10percent aq. NaOH / tetrahydrofuran / 0.5 h / 0 °C 5: 1.) KOH, 2.) Ph3P, diethyl azodicarboxylate / 1.) MeOH, 60 deg C, 3h, 2.) benzene, RT, 13h View Scheme

1: 95 percent / H2 / Lindlar catalyst / ethyl acetate / 0.5 h / Ambient temperature 2: 68 percent / Bu4NF / tetrahydrofuran / 1 h / Ambient temperature 3: 1.) DMSO/oxalyl chloride, 2.) NEt3 / 1.) CH2Cl2, -78 deg C, 30 min, 2.) -78 deg C to 0 deg C 4: 70percent ButOOH, 10percent aq. NaOH / tetrahydrofuran / 0.5 h / 0 °C 5: 1.) KOH, 2.) Ph3P, diethyl azodicarboxylate / 1.) MeOH, 60 deg C, 3h, 2.) benzene, RT, 13h View Scheme

1: 85 percent / NCS, AgNO3 / acetonitrile; H2O; CH2Cl2 / 0.12 h / 0 °C 2: 1.) Ph3P / 1.) CH2Cl2, 0 deg C, 1h, 2.) -78 deg C, 40 min 3: 1.) BuLi / 1.) THF, hexane, -78 deg C, 1h, 2.) THF, hexane, HMPA, RT, 30 min 4: 99 percent / H2 / Lindlar catalyst / ethyl acetate / 0.5 h / Ambient temperature 5: 70 percent / Bu4NF / tetrahydrofuran / 1 h / Ambient temperature 6: 1.) DMSO/oxalyl chloride, 2.) NEt3 / 1.) CH2Cl2, -78 deg C, 30 min, 2.) -78 deg C to 0 deg C 7: 70percent ButOOH, 10percent aq. NaOH / tetrahydrofuran / 0.5 h / 0 °C 8: 1.) KOH, 2.) Ph3P, diethyl azodicarboxylate / 1.) MeOH, 60 deg C, 3h, 2.) benzene, RT, 13h View Scheme

1: 85 percent / NCS, AgNO3 / acetonitrile; H2O; CH2Cl2 / 0.12 h / 0 °C 2: 1.) Ph3P / 1.) CH2Cl2, 0 deg C, 1h, 2.) -78 deg C, 40 min 3: 1.) BuLi / 1.) THF, hexane, -78 deg C, 1h, 2.) THF, hexane, HMPA, RT, 30 min 4: 95 percent / H2 / Lindlar catalyst / ethyl acetate / 0.5 h / Ambient temperature 5: 68 percent / Bu4NF / tetrahydrofuran / 1 h / Ambient temperature 6: 1.) DMSO/oxalyl chloride, 2.) NEt3 / 1.) CH2Cl2, -78 deg C, 30 min, 2.) -78 deg C to 0 deg C 7: 70percent ButOOH, 10percent aq. NaOH / tetrahydrofuran / 0.5 h / 0 °C 8: 1.) KOH, 2.) Ph3P, diethyl azodicarboxylate / 1.) MeOH, 60 deg C, 3h, 2.) benzene, RT, 13h View Scheme

1: 69 percent / p-toluenesulfonic acid / CH2Cl2 / 2 h / 100 °C 2: 65 percent / hydrogen / palladium on calcium carbonate / pentane / 1 h / 0 °C / 760 Torr View Scheme

1: 89 percent / hydrogen peroxide; aq. sodium hydroxide / diethyl ether / 2 h / 25 °C 2: 69 percent / p-toluenesulfonic acid / CH2Cl2 / 2 h / 100 °C 3: 65 percent / hydrogen / palladium on calcium carbonate / pentane / 1 h / 0 °C / 760 Torr View Scheme

1: 74.6 percent / H2 / Pb poisoned 5percent Pd/CaCO3 (Lindlar catalyst) / ethanol 2: 770 mg / conc. H2SO4 / 0.25 h / Ambient temperature 3: 1.21 g / acetic anhydride, acetic acid / Heating 4: 1.) CuI, LiI, TMSCl, 2.) n-Bu3SnH / 1.) THF, -60 deg C, 10 min, 2.) up to 0 deg C, 30 min View Scheme