1: 85 percent / Ph3P, N-chlorosuccinimide / tetrahydrofuran / 5 h / 20 °C 2: 1.) LDA / 1.) THF, hexane, -78 deg C, 40 min, 2.) THF, hexane, from -78 deg C to RT, 2 h 3: 78 percent / Li, EtNH2 / tetrahydrofuran / 4 h / -78 °C 4: 1.) Ph3P, N-chlorosuccinimide / 1.) THF, 20 deg C, 5 h, 2.) THF, 3 h 5: 98 percent / imidazole / dimethylformamide / 10 h / 50 °C 6: LDA, DABCO / tetrahydrofuran; hexane / 48 h / -78 °C 7: Bu4N+F- / tetrahydrofuran / 24 h / 15 °C 8: 70 percent / Li, EtNH2 / tetrahydrofuran / 3.5 h / -78 °C 9: 49 percent / SOCl2, pyridine / 3 h / 15 °C 10: 92 percent / MnO2 / hexane / 12 h / 15 °C View Scheme

1: 85 percent / Ph3P, N-chlorosuccinimide / tetrahydrofuran / 5 h / 20 °C 2: 1.) LDA / 1.) THF, hexane, -78 deg C, 40 min, 2.) THF, hexane, from -78 deg C to RT, 2 h 3: 78 percent / Li, EtNH2 / tetrahydrofuran / 4 h / -78 °C 4: 1.) Ph3P, N-chlorosuccinimide / 1.) THF, 20 deg C, 5 h, 2.) THF, 3 h 5: 98 percent / imidazole / dimethylformamide / 10 h / 50 °C 6: LDA, DABCO / tetrahydrofuran; hexane / 48 h / -78 °C 7: Bu4N+F- / tetrahydrofuran / 24 h / 15 °C 8: 70 percent / Li, EtNH2 / tetrahydrofuran / 3.5 h / -78 °C View Scheme

potassium hydroxide in methanol 0.0833333 h;

1: 97 percent / aq. KOH / methanol / 0.08 h 2: 74 percent / H2 / PtO2 / methanol / 2 h View Scheme

1: 89 percent / pyridine / 24 h / Ambient temperature 2: 1) Mg, CuI / 1) THF, -20 deg C, 0.5 h, 2) -15 deg C, 3 h, then 3 h, room temperature 3: 97 percent / H2 / 5percent Pd-C / ethanol / 30 h View Scheme

pyridine T=20°C; Acetylation; 6 h;

pyridine 24 h; Ambient temperature;

1: 94.5 percent / CBr4, triphenylphophine / diethyl ether / 24 h / 4 °C 2: NaH / dimethylformamide / 1.) 60 deg C, 4.5 h, 2.) 12 h, 23 deg C 3: NaCl, H2O / dimethylsulfoxide; H2O / 1.) 160 deg C, 7 h, 2.) 23 deg C, 12 h View Scheme

1: 94 percent / PBr3, pyridine / diethyl ether / 6 h / 0 °C 2: 1.) n-BuLi / 1.) THF, HMPA, hexane, -78 deg C, 1.5 h, 2.) 6 h 3: 5percent sodium amalgam, disodium hydrogen phosphate / methanol / 2 h / 0 °C 4: 91 percent / PBr3, pyridine / diethyl ether / 6 h / -5 °C View Scheme

1: 87 percent / TosOH / diethyl ether / 20 h / Ambient temperature 2: 1) Mg, CuI / 1) THF, 0.5 h, 2) -10 deg C, 4 h, then room temperature, 4 h 3: TosOH / methanol / 15 h / Ambient temperature 4: 87 percent / pyridine 5: 1) Mg, CuI / 1) THF, -15 deg C, 0.5 h, 2) -10 deg C, 4 h, then room temperature, 4 h 6: 95 percent / H2 / 5percent Pd-C / ethanol View Scheme