hydrogen; palladium on activated charcoal in ethanol P=760 Torr; 14 h;

1: 87 percent / bis(triphenylphosphine)palladium(II) chloride, Et3N / dimethylformamide / 12 h / 90 °C 2: 100 percent / H2 / Pd(OH)2 / ethanol / 12 h / 760 Torr 3: 91 percent / tetrahydrofuran / 65 h / Heating 4: 4-DMAP, EDCI / CH2Cl2 / 4 h / Ambient temperature 5: TsOH / methanol / 0.5 h / Ambient temperature 6: 100 percent / H2 / 10percent Pd/C / ethanol / 14 h / 760 Torr View Scheme

1: 34 percent / trifluoroacetic anhydride / trifluoroacetic acid / 24 h / Ambient temperature 2: 92 percent / triphenylphosphine, DIAD / tetrahydrofuran / 2 h / 0 - 20 °C 3: 85 percent / pyridine / 12 h / 0 °C 4: 87 percent / bis(triphenylphosphine)palladium(II) chloride, Et3N / dimethylformamide / 12 h / 90 °C 5: 100 percent / H2 / Pd(OH)2 / ethanol / 12 h / 760 Torr 6: 91 percent / tetrahydrofuran / 65 h / Heating 7: 4-DMAP, EDCI / CH2Cl2 / 4 h / Ambient temperature 8: TsOH / methanol / 0.5 h / Ambient temperature 9: 100 percent / H2 / 10percent Pd/C / ethanol / 14 h / 760 Torr View Scheme

1: 92 percent / triphenylphosphine, DIAD / tetrahydrofuran / 2 h / 0 - 20 °C 2: 85 percent / pyridine / 12 h / 0 °C 3: 87 percent / bis(triphenylphosphine)palladium(II) chloride, Et3N / dimethylformamide / 12 h / 90 °C 4: 100 percent / H2 / Pd(OH)2 / ethanol / 12 h / 760 Torr 5: 91 percent / tetrahydrofuran / 65 h / Heating 6: 4-DMAP, EDCI / CH2Cl2 / 4 h / Ambient temperature 7: TsOH / methanol / 0.5 h / Ambient temperature 8: 100 percent / H2 / 10percent Pd/C / ethanol / 14 h / 760 Torr View Scheme

1: 85 percent / pyridine / 12 h / 0 °C 2: 87 percent / bis(triphenylphosphine)palladium(II) chloride, Et3N / dimethylformamide / 12 h / 90 °C 3: 100 percent / H2 / Pd(OH)2 / ethanol / 12 h / 760 Torr 4: 91 percent / tetrahydrofuran / 65 h / Heating 5: 4-DMAP, EDCI / CH2Cl2 / 4 h / Ambient temperature 6: TsOH / methanol / 0.5 h / Ambient temperature 7: 100 percent / H2 / 10percent Pd/C / ethanol / 14 h / 760 Torr View Scheme

1: 100 percent / H2 / Pd(OH)2 / ethanol / 12 h / 760 Torr 2: 91 percent / tetrahydrofuran / 65 h / Heating 3: 4-DMAP, EDCI / CH2Cl2 / 4 h / Ambient temperature 4: TsOH / methanol / 0.5 h / Ambient temperature 5: 100 percent / H2 / 10percent Pd/C / ethanol / 14 h / 760 Torr View Scheme

1: 87 percent / bis(triphenylphosphine)palladium(II) chloride, Et3N / dimethylformamide / 12 h / 90 °C 2: 100 percent / H2 / Pd(OH)2 / ethanol / 12 h / 760 Torr 3: 91 percent / tetrahydrofuran / 65 h / Heating 4: 4-DMAP, EDCI / CH2Cl2 / 4 h / Ambient temperature 5: TsOH / methanol / 0.5 h / Ambient temperature 6: 100 percent / H2 / 10percent Pd/C / ethanol / 14 h / 760 Torr View Scheme

1: 4-DMAP, EDCI / CH2Cl2 / 4 h / Ambient temperature 2: TsOH / methanol / 0.5 h / Ambient temperature 3: 100 percent / H2 / 10percent Pd/C / ethanol / 14 h / 760 Torr View Scheme

1: 91 percent / tetrahydrofuran / 65 h / Heating 2: 4-DMAP, EDCI / CH2Cl2 / 4 h / Ambient temperature 3: TsOH / methanol / 0.5 h / Ambient temperature 4: 100 percent / H2 / 10percent Pd/C / ethanol / 14 h / 760 Torr View Scheme

1: 2,2-dimethyldioxirane / CH2Cl2; acetone / 0.17 h 2: K2CO3, 18-crown-6 / acetone / 8 h / Heating 3: 90 percent / NaH, tetrabutylammonium iodide / tetrahydrofuran / 6 h / Ambient temperature 4: 96 percent / TBAF / tetrahydrofuran / 4 h / Ambient temperature 5: 4-DMAP, EDCI / CH2Cl2 / 4 h / Ambient temperature 6: TsOH / methanol / 0.5 h / Ambient temperature 7: 100 percent / H2 / 10percent Pd/C / ethanol / 14 h / 760 Torr View Scheme