sodium acetate; pyridinium chlorochromate in dichloromethane 2 h;

1: 95 percent / dimethylformamide / 1.5 h / 60 °C 2: 81 percent / n-BuLi / benzene; hexane / 0 - 20 °C 3: 99 percent / H2 / Pd/C / methanol / 3 h / 1913.4 Torr 4: 96 percent / LiAlH4 / tetrahydrofuran / 1 h / 21 - 29 °C 5: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2. -65 deg C, 4 h, 2.) CH2Cl2, -65 deg C to -10 deg C, overnight View Scheme

1: 93 percent / benzene / 5 - 20 °C 2: 95 percent / dimethylformamide / 1.5 h / 60 °C 3: 81 percent / n-BuLi / benzene; hexane / 0 - 20 °C 4: 99 percent / H2 / Pd/C / methanol / 3 h / 1913.4 Torr 5: 96 percent / LiAlH4 / tetrahydrofuran / 1 h / 21 - 29 °C 6: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2. -65 deg C, 4 h, 2.) CH2Cl2, -65 deg C to -10 deg C, overnight View Scheme

1: 81 percent / n-BuLi / benzene; hexane / 0 - 20 °C 2: 99 percent / H2 / Pd/C / methanol / 3 h / 1913.4 Torr 3: 96 percent / LiAlH4 / tetrahydrofuran / 1 h / 21 - 29 °C 4: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2. -65 deg C, 4 h, 2.) CH2Cl2, -65 deg C to -10 deg C, overnight View Scheme

1: 81 percent / n-BuLi / benzene; hexane / 0 - 20 °C 2: 99 percent / H2 / Pd/C / methanol / 3 h / 1913.4 Torr 3: 96 percent / LiAlH4 / tetrahydrofuran / 1 h / 21 - 29 °C 4: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2. -65 deg C, 4 h, 2.) CH2Cl2, -65 deg C to -10 deg C, overnight View Scheme

2: CrO3, pyridine, HCl 4: p-TsOH / methanol 5: H2 / Pd/C 6: CrO3, pyridine, HCl View Scheme

1: 1.) t-BuOK / 1.) THF, 0 deg C, 20 min, 2.) THF, RT 2: H2 / 10percent Pd/C / 2942.03 Torr 3: LiAlH4 4: (COCl)2, DMSO / CH2Cl2 / 0.33 h View Scheme

1: 1.) t-BuOK / 1.) THF, 0 deg C, 20 min, 2.) THF, RT 2: H2 / 10percent Pd/C / 2942.03 Torr 3: LiAlH4 4: (COCl)2, DMSO / CH2Cl2 / 0.33 h View Scheme

1: 75 percent / 2 h / 140 °C 2: 1.) potassium tert-butoxide / 1.) THF-DMSO, 2.) r.t., occasional sonication, 50 min 3: 92 percent / hydrogen / 10 percent Pd-C / ethanol / 24 h / 2942.03 Torr / Ambient temperature 4: 1.) DMSO, oxalyl chloride, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 15 min, 2.) -78 deg C, 5 min, then r.t., 20 min View Scheme

1: 88 percent / N-bromosuccinimide, triphenylphosphine / tetrahydrofuran / 2 h / Ambient temperature 2: 75 percent / 2 h / 140 °C 3: 1.) potassium tert-butoxide / 1.) THF-DMSO, 2.) r.t., occasional sonication, 50 min 4: 92 percent / hydrogen / 10 percent Pd-C / ethanol / 24 h / 2942.03 Torr / Ambient temperature 5: 1.) DMSO, oxalyl chloride, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 15 min, 2.) -78 deg C, 5 min, then r.t., 20 min View Scheme