1: 22.6 g / potassium ferricyanide, potassium carbonate, potassium osmate dihydrate, (DHQD)2-PHAL, methanesulfonamide / H2O; 2-methyl-propan-2-ol / 18 h / Ambient temperature 2: 84 percent / tetra-n-butylammonium fluoride / tetrahydrofuran; H2O / 1.5 h / 0 °C 3: 90 percent / DMAP / pyridine / 16 h / 2 °C 4: 75 percent / sodium azide / dimethylsulfoxide / 36 h / 80 °C 5: 1.) hydrogen, 2.) sodium methoxide / 1.) palladium hydroxide on carbon / 1.) methanol, 6 h, 2.) methanol, reflux, 60 h 6: 94 percent / borane-methyl sulfide complex / tetrahydrofuran / 0 deg C, 30 min, room temperature, 2 h 7: 96 percent / conc. HCl / tetrahydrofuran / 12 h / Ambient temperature View Scheme

1: 99 percent / propionic acid / toluene / 24 h / Heating 2: 22.6 g / potassium ferricyanide, potassium carbonate, potassium osmate dihydrate, (DHQD)2-PHAL, methanesulfonamide / H2O; 2-methyl-propan-2-ol / 18 h / Ambient temperature 3: 84 percent / tetra-n-butylammonium fluoride / tetrahydrofuran; H2O / 1.5 h / 0 °C 4: 90 percent / DMAP / pyridine / 16 h / 2 °C 5: 75 percent / sodium azide / dimethylsulfoxide / 36 h / 80 °C 6: 1.) hydrogen, 2.) sodium methoxide / 1.) palladium hydroxide on carbon / 1.) methanol, 6 h, 2.) methanol, reflux, 60 h 7: 94 percent / borane-methyl sulfide complex / tetrahydrofuran / 0 deg C, 30 min, room temperature, 2 h 8: 96 percent / conc. HCl / tetrahydrofuran / 12 h / Ambient temperature View Scheme

1: 90 percent / LiCl; DBU / acetonitrile / 2 h / 20 °C 2: 99 percent / H2 / PtO2 / ethanol / 1.5 h / 20 °C / 760 Torr 3: 72 percent / Na(Hg); Na2HPO4 / methanol / 3 h / 20 °C 4: 95 percent / BH3*Me2S / tetrahydrofuran / 2.5 h / 0 - 20 °C 5: 88 percent / HCl; H2O / tetrahydrofuran / 14 h / 20 °C View Scheme

1: 98 percent / Dess-Martin periodinane; NaHCO3 / CH2Cl2 / 0.75 h / 20 °C 2: 90 percent / LiCl; DBU / acetonitrile / 2 h / 20 °C 3: 99 percent / H2 / PtO2 / ethanol / 1.5 h / 20 °C / 760 Torr 4: 72 percent / Na(Hg); Na2HPO4 / methanol / 3 h / 20 °C 5: 95 percent / BH3*Me2S / tetrahydrofuran / 2.5 h / 0 - 20 °C 6: 88 percent / HCl; H2O / tetrahydrofuran / 14 h / 20 °C View Scheme

1: 86 percent / PPh3; DIAD / tetrahydrofuran / 0.75 h / 0 °C 2: 98 percent / Dess-Martin periodinane; NaHCO3 / CH2Cl2 / 0.75 h / 20 °C 3: 90 percent / LiCl; DBU / acetonitrile / 2 h / 20 °C 4: 99 percent / H2 / PtO2 / ethanol / 1.5 h / 20 °C / 760 Torr 5: 72 percent / Na(Hg); Na2HPO4 / methanol / 3 h / 20 °C 6: 95 percent / BH3*Me2S / tetrahydrofuran / 2.5 h / 0 - 20 °C 7: 88 percent / HCl; H2O / tetrahydrofuran / 14 h / 20 °C View Scheme

1: 99 percent / H2 / PtO2 / ethanol / 1.5 h / 20 °C / 760 Torr 2: 72 percent / Na(Hg); Na2HPO4 / methanol / 3 h / 20 °C 3: 95 percent / BH3*Me2S / tetrahydrofuran / 2.5 h / 0 - 20 °C 4: 88 percent / HCl; H2O / tetrahydrofuran / 14 h / 20 °C View Scheme

1: pyridine / 2.5 h 2: 97 percent / 0.5percent aq. HCl / methanol / 1 h / Heating 3: 1.) sodium acetate; 2.) pyridine / 1.) water, 2-methoxyethanol, 25 h, reflux; 2.) 3 h 4: 1.) 2M HCl; 2.) pyridine / 1.) reflux, 13 h; 2.) overnight 5: 1.) sodium methoxide / 1.) MeOH, 2 h; 2.) conc. HCl, -15 deg C, 7 h 6: 4-dimethylaminopyridine / pyridine / 3.5 h / 70 °C 7: 1.) sodium hydride / 1.) DMF, 20 min; 2.) DMF, overnight 8: toluene-p-sulfonic acid monohydrate / methanol / 2 h 9: 77 percent / pyridine / 16 h 10: 93 percent / aq. sodium hydroxide / dioxane / 0.5 h / Heating 11: mercury(II) chloride, calcium carbonate / H2O; acetonitrile / 0.83 h 12: 2 percent / 60percent sodium hydride in mineral oil / tetrahydrofuran / 4 h 13: 70 percent / H2 / Raney nickel / ethanol / 2 h 14: 54 percent / 15M KOH / aq. ethanol / 144 h / 90 °C 15: 74 percent / lithium aluminum hydride / tetrahydrofuran / 5 h / Heating 16: 72 percent / cyclohexene / 20percent Pd(OH)2/C / ethanol / 44 h / Heating View Scheme

1: 1.) 2M HCl; 2.) pyridine / 1.) reflux, 13 h; 2.) overnight 2: 1.) sodium methoxide / 1.) MeOH, 2 h; 2.) conc. HCl, -15 deg C, 7 h 3: 4-dimethylaminopyridine / pyridine / 3.5 h / 70 °C 4: 1.) sodium hydride / 1.) DMF, 20 min; 2.) DMF, overnight 5: toluene-p-sulfonic acid monohydrate / methanol / 2 h 6: 77 percent / pyridine / 16 h 7: 93 percent / aq. sodium hydroxide / dioxane / 0.5 h / Heating 8: mercury(II) chloride, calcium carbonate / H2O; acetonitrile / 0.83 h 9: 2 percent / 60percent sodium hydride in mineral oil / tetrahydrofuran / 4 h 10: 70 percent / H2 / Raney nickel / ethanol / 2 h 11: 54 percent / 15M KOH / aq. ethanol / 144 h / 90 °C 12: 74 percent / lithium aluminum hydride / tetrahydrofuran / 5 h / Heating 13: 72 percent / cyclohexene / 20percent Pd(OH)2/C / ethanol / 44 h / Heating View Scheme

1: 97 percent / 0.5percent aq. HCl / methanol / 1 h / Heating 2: 1.) sodium acetate; 2.) pyridine / 1.) water, 2-methoxyethanol, 25 h, reflux; 2.) 3 h 3: 1.) 2M HCl; 2.) pyridine / 1.) reflux, 13 h; 2.) overnight 4: 1.) sodium methoxide / 1.) MeOH, 2 h; 2.) conc. HCl, -15 deg C, 7 h 5: 4-dimethylaminopyridine / pyridine / 3.5 h / 70 °C 6: 1.) sodium hydride / 1.) DMF, 20 min; 2.) DMF, overnight 7: toluene-p-sulfonic acid monohydrate / methanol / 2 h 8: 77 percent / pyridine / 16 h 9: 93 percent / aq. sodium hydroxide / dioxane / 0.5 h / Heating 10: mercury(II) chloride, calcium carbonate / H2O; acetonitrile / 0.83 h 11: 2 percent / 60percent sodium hydride in mineral oil / tetrahydrofuran / 4 h 12: 70 percent / H2 / Raney nickel / ethanol / 2 h 13: 54 percent / 15M KOH / aq. ethanol / 144 h / 90 °C 14: 74 percent / lithium aluminum hydride / tetrahydrofuran / 5 h / Heating 15: 72 percent / cyclohexene / 20percent Pd(OH)2/C / ethanol / 44 h / Heating View Scheme

1: 93 percent / aq. sodium hydroxide / dioxane / 0.5 h / Heating 2: mercury(II) chloride, calcium carbonate / H2O; acetonitrile / 0.83 h 3: 2 percent / 60percent sodium hydride in mineral oil / tetrahydrofuran / 4 h 4: 70 percent / H2 / Raney nickel / ethanol / 2 h 5: 54 percent / 15M KOH / aq. ethanol / 144 h / 90 °C 6: 74 percent / lithium aluminum hydride / tetrahydrofuran / 5 h / Heating 7: 72 percent / cyclohexene / 20percent Pd(OH)2/C / ethanol / 44 h / Heating View Scheme