1: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 1 h, 2.) THF, hexane, a) -20 deg C, 3 h, b) from -78 deg C to RT, 1 h 2: 1.) CuI / 1.) ether, hexane, 2.) ether, hexane, -20 deg C, 3 h 3: 79 percent / DDQ, H2O / CH2Cl2 / 3 h / Ambient temperature 4: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, from -78 deg C to RT, 3 h, 2.) CH2Cl2 5: 90 percent / tetrahydrofuran; hexane / 2 h / 0 - 20 °C View Scheme

1: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 1 h, 2.) THF, hexane, a) -20 deg C, 3 h, b) from -78 deg C to RT, 1 h 2: 1.) CuI / 1.) ether, 2.) ether, a) 0 deg C, 2 h, b) RT, 12 h 3: 91 percent / DDQ, H2O / CH2Cl2 / 2 h / Ambient temperature 4: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, from -78 deg C to RT, 2 h, 2.) CH2Cl2 View Scheme

1: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 1 h, 2.) THF, hexane, a) -20 deg C, 3 h, b) from -78 deg C to RT, 1 h 2: 1.) CuI / 1.) ether, hexane, 2.) ether, hexane, -20 deg C, 3 h 3: 79 percent / DDQ, H2O / CH2Cl2 / 3 h / Ambient temperature 4: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, from -78 deg C to RT, 3 h, 2.) CH2Cl2 View Scheme

1: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 1 h, 2.) THF, hexane, a) -20 deg C, 3 h, b) from -78 deg C to RT, 1 h 2: 1.) CuI / 1.) ether, hexane, 2.) ether, hexane, -20 deg C, 3 h 3: 79 percent / DDQ, H2O / CH2Cl2 / 3 h / Ambient temperature 4: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, from -78 deg C to RT, 3 h, 2.) CH2Cl2 5: 90 percent / tetrahydrofuran; hexane / 2 h / 0 - 20 °C View Scheme

1: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 1 h, 2.) THF, hexane, a) -20 deg C, 3 h, b) from -78 deg C to RT, 1 h 2: 1.) CuI / 1.) ether, hexane, 2.) ether, hexane, -20 deg C, 3 h 3: 79 percent / DDQ, H2O / CH2Cl2 / 3 h / Ambient temperature 4: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, from -78 deg C to RT, 3 h, 2.) CH2Cl2 5: 86 percent / MnO2, NaCN, AcOH / 3 h / Ambient temperature View Scheme

1: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 1 h, 2.) THF, hexane, a) -20 deg C, 3 h, b) from -78 deg C to RT, 1 h 2: 1.) CuI / 1.) ether, hexane, 2.) ether, hexane, -20 deg C, 3 h 3: 79 percent / DDQ, H2O / CH2Cl2 / 3 h / Ambient temperature 4: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 2 h, 2.) CH2Cl2, from -78 deg C to RT, 1 h View Scheme

Multi-step reaction with 4 steps 1: 83 percent / TiCl4 / CH2Cl2 / 1 h / Ambient temperature2: 50 percent / 1) KH, 18-crown-6 / tetrahydrofuran / 16 h / Ambient temperature3: CH3I, Na2CO3 / acetone; H2O / 60 h / Ambient temperature4: NaBH4 / ethanol / 1.5 h / -78 °C  

Multi-step reaction with 5 steps 1: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 1 h, 2.) THF, hexane, a) -20 deg C, 3 h, b) from -78 deg C to RT, 1 h2: 1.) CuI / 1.) ether, hexane, 2.) ether, hexane, -20 deg C, 3 h3: 79 percent / DDQ, H2O / CH2Cl2 / 3 h / Ambient temperature4: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 2 h, 2.) CH2Cl2, from -78 deg C to RT, 1 h5: 88 percent / MnO2, NaCN, AcOH / 3 h / Ambient temperature