tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide in dichloromethane T=25°C; 15 h; Inert atmosphere;

1: 96 percent 2: 62 percent / CrO3, 3,5-dimethylpyrazole 3: Li, liq. NH3 / ethanol 4: 93 percent / LAH 5: n-BuLi 6: n-Bu3SnH, AIBN 7: PTSA 8: 2,6-Lutidine 9: 97 percent 10: SOCl2, Py 11: TBAF / tetrahydrofuran 12: (COCl)2, DMSO, Et3N View Scheme

1: Li, liq. NH3 / ethanol 2: 93 percent / LAH 3: n-BuLi 4: n-Bu3SnH, AIBN 5: PTSA 6: 2,6-Lutidine 7: 97 percent 8: SOCl2, Py 9: TBAF / tetrahydrofuran 10: (COCl)2, DMSO, Et3N View Scheme

1: CH2Cl2 / -78 °C 2: 67 percent / H2O2, Py / CH2Cl2 3: 96 percent 4: 62 percent / CrO3, 3,5-dimethylpyrazole 5: Li, liq. NH3 / ethanol 6: 93 percent / LAH 7: n-BuLi 8: n-Bu3SnH, AIBN 9: PTSA 10: 2,6-Lutidine 11: 97 percent 12: SOCl2, Py 13: TBAF / tetrahydrofuran 14: (COCl)2, DMSO, Et3N View Scheme

1: 93 percent / LAH 2: n-BuLi 3: n-Bu3SnH, AIBN 4: PTSA 5: 2,6-Lutidine 6: 97 percent 7: SOCl2, Py 8: TBAF / tetrahydrofuran 9: (COCl)2, DMSO, Et3N View Scheme

1.1: L-phenylalanine; (1S)-10-camphorsulfonic acid / N,N-dimethyl-formamide / 20 - 70 °C / Inert atmosphere 2.1: toluene-4-sulfonic acid / benzene / 24 h / 80 °C / Inert atmosphere 3.1: ammonia; lithium / tetrahydrofuran / 1 h / -30 °C / Inert atmosphere 3.2: 3 h / Reflux 4.1: ozone / tetrahydrofuran / -78 °C / Inert atmosphere 4.2: 4 h / 25 °C / Inert atmosphere 5.1: 2,6-dimethylpyridine / dichloromethane / 1 h / -78 °C / Inert atmosphere 6.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / 18 h / 25 °C / Inert atmosphere 7.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere 7.2: 15 h / 65 °C / Inert atmosphere 8.1: palladium 10 on activated carbon; hydrogen / methanol / 12 h / 3620.13 Torr / Inert atmosphere 9.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 25 °C / Inert atmosphere 10.1: hydrogenchloride / tetrahydrofuran / 8 h / 20 °C / Inert atmosphere 11.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere 11.2: 18 h / 25 °C / Inert atmosphere 12.1: rhodium(III) trichloride hydrate / ethanol / 18 h / Inert atmosphere; Reflux 13.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / 15 h / 25 °C / Inert atmosphere View Scheme

1.1: toluene-4-sulfonic acid / benzene / 24 h / 80 °C / Inert atmosphere 2.1: ammonia; lithium / tetrahydrofuran / 1 h / -30 °C / Inert atmosphere 2.2: 3 h / Reflux 3.1: ozone / tetrahydrofuran / -78 °C / Inert atmosphere 3.2: 4 h / 25 °C / Inert atmosphere 4.1: 2,6-dimethylpyridine / dichloromethane / 1 h / -78 °C / Inert atmosphere 5.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / 18 h / 25 °C / Inert atmosphere 6.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere 6.2: 15 h / 65 °C / Inert atmosphere 7.1: palladium 10 on activated carbon; hydrogen / methanol / 12 h / 3620.13 Torr / Inert atmosphere 8.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 25 °C / Inert atmosphere 9.1: hydrogenchloride / tetrahydrofuran / 8 h / 20 °C / Inert atmosphere 10.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere 10.2: 18 h / 25 °C / Inert atmosphere 11.1: rhodium(III) trichloride hydrate / ethanol / 18 h / Inert atmosphere; Reflux 12.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / 15 h / 25 °C / Inert atmosphere View Scheme

1.1: ammonia; lithium / tetrahydrofuran / 1 h / -30 °C / Inert atmosphere 1.2: 3 h / Reflux 2.1: ozone / tetrahydrofuran / -78 °C / Inert atmosphere 2.2: 4 h / 25 °C / Inert atmosphere 3.1: 2,6-dimethylpyridine / dichloromethane / 1 h / -78 °C / Inert atmosphere 4.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / 18 h / 25 °C / Inert atmosphere 5.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere 5.2: 15 h / 65 °C / Inert atmosphere 6.1: palladium 10 on activated carbon; hydrogen / methanol / 12 h / 3620.13 Torr / Inert atmosphere 7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 25 °C / Inert atmosphere 8.1: hydrogenchloride / tetrahydrofuran / 8 h / 20 °C / Inert atmosphere 9.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere 9.2: 18 h / 25 °C / Inert atmosphere 10.1: rhodium(III) trichloride hydrate / ethanol / 18 h / Inert atmosphere; Reflux 11.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / 15 h / 25 °C / Inert atmosphere View Scheme

1.1: palladium 10 on activated carbon; hydrogen / methanol / 12 h / 3620.13 Torr / Inert atmosphere 2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 25 °C / Inert atmosphere 3.1: hydrogenchloride / tetrahydrofuran / 8 h / 20 °C / Inert atmosphere 4.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere 4.2: 18 h / 25 °C / Inert atmosphere 5.1: rhodium(III) trichloride hydrate / ethanol / 18 h / Inert atmosphere; Reflux 6.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / 15 h / 25 °C / Inert atmosphere View Scheme

1: TBAF / tetrahydrofuran 2: (COCl)2, DMSO, Et3N View Scheme