1: 83 percent / aq. HOAc 2: 94 percent / NaBH4 / methanol / 0 °C 3: 95 percent / CBr4, PPh3 / dimethylformamide / 0 °C 4: 77 percent / acetonitrile / Heating 5: 1.) n-BuLi, LiBr, KOCMe3, 2.) HCl, 3.) LiOH / 1.) THF, -78 deg C, 2.) THF, room temperature, 10 h, 3.) MeOH, H2O, 10 h 6: 1.) 2,4,6-trichlorobenzoyl chloride, Et3N, DMAP, 2.) TiCl4 / 1.) THF, toluene, reflux, 6 h, 2.) CH2Cl2, 0 deg C, 2 h View Scheme

1: 1.) K-Selectride, 2.) i-Pr2NEt / 1.) THF, -78 deg C, 1 h, 2.) CH2Cl2, 10 h 2: 58 percent / MeI, NaHCO3 / acetonitrile; H2O / Ambient temperature 3: 1.) n-BuLi, LiBr, KOCMe3, 2.) HCl, 3.) LiOH / 1.) THF, -78 deg C, 2.) THF, room temperature, 10 h, 3.) MeOH, H2O, 10 h 4: 1.) 2,4,6-trichlorobenzoyl chloride, Et3N, DMAP, 2.) TiCl4 / 1.) THF, toluene, reflux, 6 h, 2.) CH2Cl2, 0 deg C, 2 h View Scheme

1: 2.) i-Pr2NEt / 2.) CH2Cl2, 12 h 2: 1.) K-Selectride, 2.) i-Pr2NEt / 1.) THF, -78 deg C, 1 h, 2.) CH2Cl2, 10 h 3: 58 percent / MeI, NaHCO3 / acetonitrile; H2O / Ambient temperature 4: 1.) n-BuLi, LiBr, KOCMe3, 2.) HCl, 3.) LiOH / 1.) THF, -78 deg C, 2.) THF, room temperature, 10 h, 3.) MeOH, H2O, 10 h 5: 1.) 2,4,6-trichlorobenzoyl chloride, Et3N, DMAP, 2.) TiCl4 / 1.) THF, toluene, reflux, 6 h, 2.) CH2Cl2, 0 deg C, 2 h View Scheme

1: 58 percent / MeI, NaHCO3 / acetonitrile; H2O / Ambient temperature 2: 1.) n-BuLi, LiBr, KOCMe3, 2.) HCl, 3.) LiOH / 1.) THF, -78 deg C, 2.) THF, room temperature, 10 h, 3.) MeOH, H2O, 10 h 3: 1.) 2,4,6-trichlorobenzoyl chloride, Et3N, DMAP, 2.) TiCl4 / 1.) THF, toluene, reflux, 6 h, 2.) CH2Cl2, 0 deg C, 2 h View Scheme

1: PPTS / methanol 2: NaBH4 / methanol / -78 °C View Scheme

1.1: 2,4,6-trichlorobenzoyl chloride; Et3N / tetrahydrofuran / 2 h / 20 °C 1.2: 51 percent / 4-DMAP / toluene / 24 h / Heating 2.1: 95 percent / NaBH4 / methanol / -78 °C View Scheme

1.1: aq. HCl / tetrahydrofuran 2.1: LiOH 3.1: 2,4,6-trichlorobenzoyl chloride; Et3N / tetrahydrofuran / 2 h / 20 °C 3.2: 51 percent / 4-DMAP / toluene / 24 h / Heating 4.1: 95 percent / NaBH4 / methanol / -78 °C View Scheme

1: 100 percent / PPh3, diethyl azodicarboxylate / tetrahydrofuran / 20 h / Ambient temperature 2: 87 percent / thiourea, NaHCO3 / ethanol / 2 h / 95 °C 3: 91 percent / i-Pr2EtN / CH2Cl2 / 24 h 4: 100 percent / diisobutylaluminium hydride / tetrahydrofuran / 2 h / -78 °C 5: 80 percent / toluene / 6 h / 95 °C 6: 60 percent / pyridinium chlorochromate, toluene-p-sulfonic acid / CH2Cl2 / 12 h / Ambient temperature 7: 87 percent / MeLi, CuCN / tetrahydrofuran / 0.5 h / -78 °C 8: 50 percent / DIBAL-H / diethyl ether / 1 h / -78 °C 9: 87 percent / i-Pr2EtN / CH2Cl2 / 12 h / Ambient temperature 10: 1.) aq. HCl, 2.) LiOH / 1.) THF, room temperature, 14 h, 2.) H2O, MeOH, room temperature, 10 h 11: 1.) Et3N, 2,4,6-trichlorobenzoyl chloride, 2.) N,N-dimethylaminopyridine / 1.) THF, room temperature, 6 h, 2.) toluene, reflux, 14 h 12: 85 percent / TiCl4 / CH2Cl2 / 2 h / 0 °C View Scheme

1: 91 percent / i-Pr2EtN / CH2Cl2 / 24 h 2: 100 percent / diisobutylaluminium hydride / tetrahydrofuran / 2 h / -78 °C 3: 80 percent / toluene / 6 h / 95 °C 4: 60 percent / pyridinium chlorochromate, toluene-p-sulfonic acid / CH2Cl2 / 12 h / Ambient temperature 5: 87 percent / MeLi, CuCN / tetrahydrofuran / 0.5 h / -78 °C 6: 50 percent / DIBAL-H / diethyl ether / 1 h / -78 °C 7: 87 percent / i-Pr2EtN / CH2Cl2 / 12 h / Ambient temperature 8: 1.) aq. HCl, 2.) LiOH / 1.) THF, room temperature, 14 h, 2.) H2O, MeOH, room temperature, 10 h 9: 1.) Et3N, 2,4,6-trichlorobenzoyl chloride, 2.) N,N-dimethylaminopyridine / 1.) THF, room temperature, 6 h, 2.) toluene, reflux, 14 h 10: 85 percent / TiCl4 / CH2Cl2 / 2 h / 0 °C View Scheme

1: 85 percent / Na / tetrahydrofuran; liquid ammonia / 1.5 h / -35 - -30 °C 2: 17 g / pyridine / 8 h / 0 °C 3: 74 percent / NaHCO3, NaI / acetone / 40 h / Heating 4: 82 percent / n-BuLi / hexamethylphosphoric acid triamide; tetrahydrofuran; hexane / 1 h / Ambient temperature 5: 79 percent / Na / tetrahydrofuran; liquid ammonia / 1 h 6: 431 mg / PCC, NaOAc / CH2Cl2 / 2.5 h / Ambient temperature 7: 570 mg / diisopropylamine / dimethylsulfoxide / Ambient temperature 8: 54 percent / pyrrolidine / hexamethylphosphoric acid triamide / Ambient temperature 9: 97 percent / PPTS / CH2Cl2 / Ambient temperature 10: 98 percent / 0.13N LiOH / methanol; H2O / 18 h / 50 °C 11: 93 percent / n-Bu4NF / tetrahydrofuran / 5 h / Ambient temperature 12: 47 percent / triphenylphosphine, dipyridyl disulfide / xylene / Ambient temperature 13: 35 mg / acetic acid; tetrahydrofuran; H2O / 4 h / 50 °C 14: TiCl4 / CH2Cl2 / 0.25 h / 0 °C View Scheme