1: 1N NaOH / tetrahydrofuran; methanol / 2 h / 20 °C 2: 1) LDA / 1) THF, -78 deg C, 1 h, 2) -78 deg C to 0 deg C, 2 h 3: DCC, DMAP, Et3N / CH2Cl2 / 2 h / 20 °C 4: nBu4NF / tetrahydrofuran / 2 h / 20 °C 5: 92 percent / Jones' reagent / acetone / 0.17 h / 0 °C 6: MeONa / methanol / 1 h / 20 °C 7: 1) nBuLi / 1) THF, hexane, -20 deg C, 20 min, 2a) -78 deg C to -20 deg C, 30 min, b) -20 deg C, 15 min 8: 65 percent / PPh3 / Pd(OAc)2 / toluene / 1 h / 100 °C View Scheme

1: nBu4NF / tetrahydrofuran / 2 h / 20 °C 2: 92 percent / Jones' reagent / acetone / 0.17 h / 0 °C 3: MeONa / methanol / 1 h / 20 °C 4: 1) nBuLi / 1) THF, hexane, -20 deg C, 20 min, 2a) -78 deg C to -20 deg C, 30 min, b) -20 deg C, 15 min 5: 65 percent / PPh3 / Pd(OAc)2 / toluene / 1 h / 100 °C View Scheme

1: 84 percent / RuCl3*3H2O, NaIO4 / acetonitrile; CCl4; H2O / 24 h / 20 °C 2: MeONa / methanol / 15 h / Heating 3: 95 percent / triethylamine, 4-dimethylaminopyridine / dimethylformamide / 6 h / 20 °C 4: 1N NaOH / tetrahydrofuran; methanol / 2 h / 20 °C 5: 1) LDA / 1) THF, -78 deg C, 1 h, 2) -78 deg C to 0 deg C, 2 h 6: DCC, DMAP, Et3N / CH2Cl2 / 2 h / 20 °C 7: nBu4NF / tetrahydrofuran / 2 h / 20 °C 8: 92 percent / Jones' reagent / acetone / 0.17 h / 0 °C 9: MeONa / methanol / 1 h / 20 °C 10: 1) nBuLi / 1) THF, hexane, -20 deg C, 20 min, 2a) -78 deg C to -20 deg C, 30 min, b) -20 deg C, 15 min 11: 65 percent / PPh3 / Pd(OAc)2 / toluene / 1 h / 100 °C View Scheme

1: MeONa / methanol / 15 h / Heating 2: 95 percent / triethylamine, 4-dimethylaminopyridine / dimethylformamide / 6 h / 20 °C 3: 1N NaOH / tetrahydrofuran; methanol / 2 h / 20 °C 4: 1) LDA / 1) THF, -78 deg C, 1 h, 2) -78 deg C to 0 deg C, 2 h 5: DCC, DMAP, Et3N / CH2Cl2 / 2 h / 20 °C 6: nBu4NF / tetrahydrofuran / 2 h / 20 °C 7: 92 percent / Jones' reagent / acetone / 0.17 h / 0 °C 8: MeONa / methanol / 1 h / 20 °C 9: 1) nBuLi / 1) THF, hexane, -20 deg C, 20 min, 2a) -78 deg C to -20 deg C, 30 min, b) -20 deg C, 15 min 10: 65 percent / PPh3 / Pd(OAc)2 / toluene / 1 h / 100 °C View Scheme

1: 1.) NaH / 1.) THF, RT, 1 h, 2.) THF, RT, 3 h 2: 68 percent / RuCl3, NaIO4, H2O / ethyl acetate; acetonitrile / 0.25 h / 0 °C 3: 85 percent / p-TsOH / CH2Cl2 / 1.) RT, 2 h, 2.) reflux, 2.5 h 4: 70 percent / SmI2, HMPA, ethylene glycol / tetrahydrofuran / 3.5 h / Ambient temperature 5: 1.) DMSO, (CF3CO)2O, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 15 min, 2.) CH2Cl2, -78 deg C, 30 min 6: 1.) NaH, HMPA / 1.) THF, 0 deg C, 1 h, 2.) THF, RT, 6.5 h 7: tetrabutylammonium fluoride / tetrahydrofuran / 2.5 h / 0 °C 8: 77 percent / PCC, AcONa, molecular sieves 3 Angstroem / CH2Cl2 / 1 h / Ambient temperature 9: 1.) n-BuLi / 1.) THF, -20 deg C, 15 min, 2.) THF, -20 deg C, 3 h 10: 1.) DMSO, (CF3CO)2O, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 30 min, 2.) CH2Cl2, -78 deg C, 1 h 11: 88 percent / Ph3P / toluene / 8.5 h / Heating 12: 62 percent / 5percent HCl / methanol / 10 h / Ambient temperature View Scheme

1: 68 percent / RuCl3, NaIO4, H2O / ethyl acetate; acetonitrile / 0.25 h / 0 °C 2: 85 percent / p-TsOH / CH2Cl2 / 1.) RT, 2 h, 2.) reflux, 2.5 h 3: 70 percent / SmI2, HMPA, ethylene glycol / tetrahydrofuran / 3.5 h / Ambient temperature 4: 1.) DMSO, (CF3CO)2O, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 15 min, 2.) CH2Cl2, -78 deg C, 30 min 5: 1.) NaH, HMPA / 1.) THF, 0 deg C, 1 h, 2.) THF, RT, 6.5 h 6: tetrabutylammonium fluoride / tetrahydrofuran / 2.5 h / 0 °C 7: 77 percent / PCC, AcONa, molecular sieves 3 Angstroem / CH2Cl2 / 1 h / Ambient temperature 8: 1.) n-BuLi / 1.) THF, -20 deg C, 15 min, 2.) THF, -20 deg C, 3 h 9: 1.) DMSO, (CF3CO)2O, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 30 min, 2.) CH2Cl2, -78 deg C, 1 h 10: 88 percent / Ph3P / toluene / 8.5 h / Heating 11: 62 percent / 5percent HCl / methanol / 10 h / Ambient temperature View Scheme

1: 85 percent / p-TsOH / CH2Cl2 / 1.) RT, 2 h, 2.) reflux, 2.5 h 2: 70 percent / SmI2, HMPA, ethylene glycol / tetrahydrofuran / 3.5 h / Ambient temperature 3: 1.) DMSO, (CF3CO)2O, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 15 min, 2.) CH2Cl2, -78 deg C, 30 min 4: 1.) NaH, HMPA / 1.) THF, 0 deg C, 1 h, 2.) THF, RT, 6.5 h 5: tetrabutylammonium fluoride / tetrahydrofuran / 2.5 h / 0 °C 6: 77 percent / PCC, AcONa, molecular sieves 3 Angstroem / CH2Cl2 / 1 h / Ambient temperature 7: 1.) n-BuLi / 1.) THF, -20 deg C, 15 min, 2.) THF, -20 deg C, 3 h 8: 1.) DMSO, (CF3CO)2O, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 30 min, 2.) CH2Cl2, -78 deg C, 1 h 9: 88 percent / Ph3P / toluene / 8.5 h / Heating 10: 62 percent / 5percent HCl / methanol / 10 h / Ambient temperature View Scheme

1: 77 percent / PCC, AcONa, molecular sieves 3 Angstroem / CH2Cl2 / 1 h / Ambient temperature 2: 1.) n-BuLi / 1.) THF, -20 deg C, 15 min, 2.) THF, -20 deg C, 3 h 3: 1.) DMSO, (CF3CO)2O, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 30 min, 2.) CH2Cl2, -78 deg C, 1 h 4: 88 percent / Ph3P / toluene / 8.5 h / Heating 5: 62 percent / 5percent HCl / methanol / 10 h / Ambient temperature View Scheme

1: 1.) n-BuLi / 1.) THF, -20 deg C, 15 min, 2.) THF, -20 deg C, 3 h 2: 1.) DMSO, (CF3CO)2O, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 30 min, 2.) CH2Cl2, -78 deg C, 1 h 3: 88 percent / Ph3P / toluene / 8.5 h / Heating 4: 62 percent / 5percent HCl / methanol / 10 h / Ambient temperature View Scheme

1: 1.) DMSO, (CF3CO)2O, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 15 min, 2.) CH2Cl2, -78 deg C, 30 min 2: 1.) NaH, HMPA / 1.) THF, 0 deg C, 1 h, 2.) THF, RT, 6.5 h 3: tetrabutylammonium fluoride / tetrahydrofuran / 2.5 h / 0 °C 4: 77 percent / PCC, AcONa, molecular sieves 3 Angstroem / CH2Cl2 / 1 h / Ambient temperature 5: 1.) n-BuLi / 1.) THF, -20 deg C, 15 min, 2.) THF, -20 deg C, 3 h 6: 1.) DMSO, (CF3CO)2O, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 30 min, 2.) CH2Cl2, -78 deg C, 1 h 7: 88 percent / Ph3P / toluene / 8.5 h / Heating 8: 62 percent / 5percent HCl / methanol / 10 h / Ambient temperature View Scheme