1: 60 percent / NEt3, NaI / acetonitrile / 15 h / 85 °C 2: 80 percent / NaN(SiMe3)2 / tetrahydrofuran / -100 deg C to RT 3: TsOH / tetrahydrofuran; H2O / 0.17 h 4: 50 percent / NaN(SiMe3)2 / tetrahydrofuran / -100 deg C to RT View Scheme

1: 100 percent / calcium carbonate / acetonitrile / 72 h / 40 °C 2: 1.) n-BuLi / 1) THF, hexane, -45 deg C, 30 min; 2) THF, hexane, HMPA, -78 deg C, 30 min; 3) THF, hexane, HMPA, -78 deg C --> rt 3: 98 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 0.5 h / Ambient temperature 4: 95 percent / Ph3P, imidazole iodine / tetrahydrofuran / 1 h / Ambient temperature 5: 100 percent / calcium carbonate / acetonitrile / 72 h / 50 °C 6: 1.) n-BuLi / 1) THF, hexane, -78 --> -40 deg C, 45 min; 2) THF, HMPA, hexane, -78 deg C --> rt, 90 min 7: 100 percent / aq. CF3CO2H / CH2Cl2 / 0.5 h / 0 °C 8: 1.) n-BuLi / 1) THF, hexane, -78 deg C --> rt; 2) THF, hexane, HMPA, -78 deg C --> rt, 60 min View Scheme

1: 96 percent / Ph3P, imidazole, I2 / tetrahydrofuran / -30 - 20 °C 2: 100 percent / calcium carbonate / acetonitrile / 72 h / 40 °C 3: 1.) n-BuLi / 1) THF, hexane, -45 deg C, 30 min; 2) THF, hexane, HMPA, -78 deg C, 30 min; 3) THF, hexane, HMPA, -78 deg C --> rt 4: 98 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 0.5 h / Ambient temperature 5: 95 percent / Ph3P, imidazole iodine / tetrahydrofuran / 1 h / Ambient temperature 6: 100 percent / calcium carbonate / acetonitrile / 72 h / 50 °C 7: 1.) n-BuLi / 1) THF, hexane, -78 --> -40 deg C, 45 min; 2) THF, HMPA, hexane, -78 deg C --> rt, 90 min 8: 100 percent / aq. CF3CO2H / CH2Cl2 / 0.5 h / 0 °C 9: 1.) n-BuLi / 1) THF, hexane, -78 deg C --> rt; 2) THF, hexane, HMPA, -78 deg C --> rt, 60 min View Scheme

1: 95 percent / Ph3P, imidazole iodine / tetrahydrofuran / 1 h / Ambient temperature 2: 100 percent / calcium carbonate / acetonitrile / 72 h / 50 °C 3: 1.) n-BuLi / 1) THF, hexane, -78 --> -40 deg C, 45 min; 2) THF, HMPA, hexane, -78 deg C --> rt, 90 min 4: 100 percent / aq. CF3CO2H / CH2Cl2 / 0.5 h / 0 °C 5: 1.) n-BuLi / 1) THF, hexane, -78 deg C --> rt; 2) THF, hexane, HMPA, -78 deg C --> rt, 60 min View Scheme

1: 100 percent / calcium carbonate / acetonitrile / 72 h / 50 °C 2: 1.) n-BuLi / 1) THF, hexane, -78 --> -40 deg C, 45 min; 2) THF, HMPA, hexane, -78 deg C --> rt, 90 min 3: 100 percent / aq. CF3CO2H / CH2Cl2 / 0.5 h / 0 °C 4: 1.) n-BuLi / 1) THF, hexane, -78 deg C --> rt; 2) THF, hexane, HMPA, -78 deg C --> rt, 60 min View Scheme

1: 100 percent / aq. CF3CO2H / CH2Cl2 / 0.5 h / 0 °C 2: 1.) n-BuLi / 1) THF, hexane, -78 deg C --> rt; 2) THF, hexane, HMPA, -78 deg C --> rt, 60 min View Scheme

1: 98 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 0.5 h / Ambient temperature 2: 95 percent / Ph3P, imidazole iodine / tetrahydrofuran / 1 h / Ambient temperature 3: 100 percent / calcium carbonate / acetonitrile / 72 h / 50 °C 4: 1.) n-BuLi / 1) THF, hexane, -78 --> -40 deg C, 45 min; 2) THF, HMPA, hexane, -78 deg C --> rt, 90 min 5: 100 percent / aq. CF3CO2H / CH2Cl2 / 0.5 h / 0 °C 6: 1.) n-BuLi / 1) THF, hexane, -78 deg C --> rt; 2) THF, hexane, HMPA, -78 deg C --> rt, 60 min View Scheme

1: Lypase type XIII / dioxane; H2O / 4 h / 37 °C View Scheme

acetyl chloride T=20°C; 1.5 h; Inert atmosphere;

1: (i) EtMgBr, THF, Et2O, (ii) /BRN= 1817367/, CuCl 2: H2 / Lindlar catalyst / 0 °C / 760 Torr View Scheme