1: N-Boc-deacetylcolchicine With hydrogenchloride in diethyl ether T=20°C; 1 h; 2: acetic anhydride With 4-(N,N-dimethlyamino)pyridine; triethylamine in diethyl ether T=25°C; 10 h;

1.1: 98 percent / 2,6-lutidine / CH2Cl2 / 5 h / 20 °C 2.1: 95 percent / silver trifluoroacetate; I2; sodium bicarbonate / CHCl3 / 3 h / 0 °C 3.1: 92 percent / Et2NH; bis[triphenylphosphine]palladium dichloride; copper(I) iodide / dimethylsulfoxide / 20 h / 90 °C 4.1: 98 percent / n-Bu4NF / tetrahydrofuran / 7 h / 20 °C 5.1: 96 percent / oxalyl chloride; DMSO / CH2Cl2 / 0.75 h / -78 °C 6.1: BH3*THF / tetrahydrofuran / 1 h / 20 °C 6.2: t-BuLi / pentane; tetrahydrofuran / 0.67 h / -78 °C 6.3: 64 percent / tetrahydrofuran; pentane / 3 h / -78 °C 7.1: 96 percent / oxalyl chloride; DMSO / CH2Cl2 / 0.5 h / -78 °C 8.1: 85 percent / BH3*THF; (S)-(-)-2-amino-3-methyl-1,1-diphenylbutan-1-ol / tetrahydrofuran / 6 h / 23 °C 9.1: 60 percent / diphenylphosphoryl azide; triphenylphosphine; diisopropylazodicarboxylate / tetrahydrofuran / 12 h / 20 °C 10.1: 95 percent / Ph3P / tetrahydrofuran; H2O / 50 h / 20 °C 11.1: 98 percent / DMAP; Et3N / diethyl ether / 7 h / 20 °C 12.1: 60 percent / various solvent(s) / 66 h / Heating 13.1: 99 percent / Et3N; 4-(dimethylamino)pyridine / CH2Cl2 / 10 h / 35 °C 14.1: 99 percent / aq. LiOH / tetrahydrofuran / 12 h 15.1: 45 percent Turnov. / trimethylsilyltriflate / various solvent(s) / -78 - -60 °C 16.1: 62 percent / Et3N; trimethylsilyl triflate / CH2Cl2 / 2 h / 0 °C 17.1: HCl / diethyl ether / 1 h / 20 °C 17.2: 98 percent / 4-(dimethylamino)pyridine; Et3N / diethyl ether / 10 h / 25 °C View Scheme

1.1: 95 percent / silver trifluoroacetate; I2; sodium bicarbonate / CHCl3 / 3 h / 0 °C 2.1: 92 percent / Et2NH; bis[triphenylphosphine]palladium dichloride; copper(I) iodide / dimethylsulfoxide / 20 h / 90 °C 3.1: 98 percent / n-Bu4NF / tetrahydrofuran / 7 h / 20 °C 4.1: 96 percent / oxalyl chloride; DMSO / CH2Cl2 / 0.75 h / -78 °C 5.1: BH3*THF / tetrahydrofuran / 1 h / 20 °C 5.2: t-BuLi / pentane; tetrahydrofuran / 0.67 h / -78 °C 5.3: 64 percent / tetrahydrofuran; pentane / 3 h / -78 °C 6.1: 96 percent / oxalyl chloride; DMSO / CH2Cl2 / 0.5 h / -78 °C 7.1: 85 percent / BH3*THF; (S)-(-)-2-amino-3-methyl-1,1-diphenylbutan-1-ol / tetrahydrofuran / 6 h / 23 °C 8.1: 60 percent / diphenylphosphoryl azide; triphenylphosphine; diisopropylazodicarboxylate / tetrahydrofuran / 12 h / 20 °C 9.1: 95 percent / Ph3P / tetrahydrofuran; H2O / 50 h / 20 °C 10.1: 98 percent / DMAP; Et3N / diethyl ether / 7 h / 20 °C 11.1: 60 percent / various solvent(s) / 66 h / Heating 12.1: 99 percent / Et3N; 4-(dimethylamino)pyridine / CH2Cl2 / 10 h / 35 °C 13.1: 99 percent / aq. LiOH / tetrahydrofuran / 12 h 14.1: 45 percent Turnov. / trimethylsilyltriflate / various solvent(s) / -78 - -60 °C 15.1: 62 percent / Et3N; trimethylsilyl triflate / CH2Cl2 / 2 h / 0 °C 16.1: HCl / diethyl ether / 1 h / 20 °C 16.2: 98 percent / 4-(dimethylamino)pyridine; Et3N / diethyl ether / 10 h / 25 °C View Scheme

1.1: 92 percent / Et2NH; bis[triphenylphosphine]palladium dichloride; copper(I) iodide / dimethylsulfoxide / 20 h / 90 °C 2.1: 98 percent / n-Bu4NF / tetrahydrofuran / 7 h / 20 °C 3.1: 96 percent / oxalyl chloride; DMSO / CH2Cl2 / 0.75 h / -78 °C 4.1: BH3*THF / tetrahydrofuran / 1 h / 20 °C 4.2: t-BuLi / pentane; tetrahydrofuran / 0.67 h / -78 °C 4.3: 64 percent / tetrahydrofuran; pentane / 3 h / -78 °C 5.1: 96 percent / oxalyl chloride; DMSO / CH2Cl2 / 0.5 h / -78 °C 6.1: 85 percent / BH3*THF; (S)-(-)-2-amino-3-methyl-1,1-diphenylbutan-1-ol / tetrahydrofuran / 6 h / 23 °C 7.1: 60 percent / diphenylphosphoryl azide; triphenylphosphine; diisopropylazodicarboxylate / tetrahydrofuran / 12 h / 20 °C 8.1: 95 percent / Ph3P / tetrahydrofuran; H2O / 50 h / 20 °C 9.1: 98 percent / DMAP; Et3N / diethyl ether / 7 h / 20 °C 10.1: 60 percent / various solvent(s) / 66 h / Heating 11.1: 99 percent / Et3N; 4-(dimethylamino)pyridine / CH2Cl2 / 10 h / 35 °C 12.1: 99 percent / aq. LiOH / tetrahydrofuran / 12 h 13.1: 45 percent Turnov. / trimethylsilyltriflate / various solvent(s) / -78 - -60 °C 14.1: 62 percent / Et3N; trimethylsilyl triflate / CH2Cl2 / 2 h / 0 °C 15.1: HCl / diethyl ether / 1 h / 20 °C 15.2: 98 percent / 4-(dimethylamino)pyridine; Et3N / diethyl ether / 10 h / 25 °C View Scheme

in tetrahydrofuran 5 h;

in methanol

1.1: zinc-copper couple / benzene; N,N-dimethyl-acetamide / 3 h / 20 °C / sonication 1.2: 31 percent / bis(triphenylphosphine)palladium dichloride / benzene; N,N-dimethyl-acetamide / 2 h / sonication 2.1: 91 percent / H2 / Pd/C / ethanol; H2O / 22 h / 3102.89 Torr 3.1: 93 percent / NaHCO3; silver trifluoroacetate; I2 / CHCl3 / 2 h / 0 °C 4.1: trifluoroacetic acid / diethyl ether / 3 h / 20 °C 5.1: 454 mg / 4-(dimethylamino)pyridine; Et3N / diethyl ether / 10 h 6.1: 60 percent / Et2NH; bis[triphenylphosphine]palladium dichloride; copper(I) iodide / dimethylsulfoxide / 15 h / 90 °C 7.1: 91 percent / potassium carbonate / methanol / 11 h / 20 °C 8.1: 100 percent / DIBAL / CH2Cl2; hexane / 1 h / -78 °C 9.1: potassium carbonate / methanol / 1 h / Heating 9.2: 64 percent / KOH / methanol / 3 h / Heating 10.1: 70 percent / various solvent(s) / 40 h / Heating 11.1: 99 percent / Et3N; 4-(dimethylamino)pyridine / CH2Cl2 / 10 h / 35 °C 12.1: 99 percent / aq. LiOH / tetrahydrofuran / 12 h 13.1: 45 percent Turnov. / trimethylsilyltriflate / various solvent(s) / -78 - -60 °C 14.1: 62 percent / Et3N; trimethylsilyl triflate / CH2Cl2 / 2 h / 0 °C 15.1: HCl / diethyl ether / 1 h / 20 °C 15.2: 98 percent / 4-(dimethylamino)pyridine; Et3N / diethyl ether / 10 h / 25 °C View Scheme

1.1: 91 percent / H2 / Pd/C / ethanol; H2O / 22 h / 3102.89 Torr 2.1: 93 percent / NaHCO3; silver trifluoroacetate; I2 / CHCl3 / 2 h / 0 °C 3.1: trifluoroacetic acid / diethyl ether / 3 h / 20 °C 4.1: 454 mg / 4-(dimethylamino)pyridine; Et3N / diethyl ether / 10 h 5.1: 60 percent / Et2NH; bis[triphenylphosphine]palladium dichloride; copper(I) iodide / dimethylsulfoxide / 15 h / 90 °C 6.1: 91 percent / potassium carbonate / methanol / 11 h / 20 °C 7.1: 100 percent / DIBAL / CH2Cl2; hexane / 1 h / -78 °C 8.1: potassium carbonate / methanol / 1 h / Heating 8.2: 64 percent / KOH / methanol / 3 h / Heating 9.1: 70 percent / various solvent(s) / 40 h / Heating 10.1: 99 percent / Et3N; 4-(dimethylamino)pyridine / CH2Cl2 / 10 h / 35 °C 11.1: 99 percent / aq. LiOH / tetrahydrofuran / 12 h 12.1: 45 percent Turnov. / trimethylsilyltriflate / various solvent(s) / -78 - -60 °C 13.1: 62 percent / Et3N; trimethylsilyl triflate / CH2Cl2 / 2 h / 0 °C 14.1: HCl / diethyl ether / 1 h / 20 °C 14.2: 98 percent / 4-(dimethylamino)pyridine; Et3N / diethyl ether / 10 h / 25 °C View Scheme

1.1: BH3*THF / tetrahydrofuran / 1 h / 20 °C 1.2: t-BuLi / pentane; tetrahydrofuran / 0.67 h / -78 °C 1.3: 64 percent / tetrahydrofuran; pentane / 3 h / -78 °C 2.1: 96 percent / oxalyl chloride; DMSO / CH2Cl2 / 0.5 h / -78 °C 3.1: 85 percent / BH3*THF; (S)-(-)-2-amino-3-methyl-1,1-diphenylbutan-1-ol / tetrahydrofuran / 6 h / 23 °C 4.1: 60 percent / diphenylphosphoryl azide; triphenylphosphine; diisopropylazodicarboxylate / tetrahydrofuran / 12 h / 20 °C 5.1: 95 percent / Ph3P / tetrahydrofuran; H2O / 50 h / 20 °C 6.1: 98 percent / DMAP; Et3N / diethyl ether / 7 h / 20 °C 7.1: 60 percent / various solvent(s) / 66 h / Heating 8.1: 99 percent / Et3N; 4-(dimethylamino)pyridine / CH2Cl2 / 10 h / 35 °C 9.1: 99 percent / aq. LiOH / tetrahydrofuran / 12 h 10.1: 45 percent Turnov. / trimethylsilyltriflate / various solvent(s) / -78 - -60 °C 11.1: 62 percent / Et3N; trimethylsilyl triflate / CH2Cl2 / 2 h / 0 °C 12.1: HCl / diethyl ether / 1 h / 20 °C 12.2: 98 percent / 4-(dimethylamino)pyridine; Et3N / diethyl ether / 10 h / 25 °C View Scheme

1.1: 96 percent / oxalyl chloride; DMSO / CH2Cl2 / 0.75 h / -78 °C 2.1: BH3*THF / tetrahydrofuran / 1 h / 20 °C 2.2: t-BuLi / pentane; tetrahydrofuran / 0.67 h / -78 °C 2.3: 64 percent / tetrahydrofuran; pentane / 3 h / -78 °C 3.1: 96 percent / oxalyl chloride; DMSO / CH2Cl2 / 0.5 h / -78 °C 4.1: 85 percent / BH3*THF; (S)-(-)-2-amino-3-methyl-1,1-diphenylbutan-1-ol / tetrahydrofuran / 6 h / 23 °C 5.1: 60 percent / diphenylphosphoryl azide; triphenylphosphine; diisopropylazodicarboxylate / tetrahydrofuran / 12 h / 20 °C 6.1: 95 percent / Ph3P / tetrahydrofuran; H2O / 50 h / 20 °C 7.1: 98 percent / DMAP; Et3N / diethyl ether / 7 h / 20 °C 8.1: 60 percent / various solvent(s) / 66 h / Heating 9.1: 99 percent / Et3N; 4-(dimethylamino)pyridine / CH2Cl2 / 10 h / 35 °C 10.1: 99 percent / aq. LiOH / tetrahydrofuran / 12 h 11.1: 45 percent Turnov. / trimethylsilyltriflate / various solvent(s) / -78 - -60 °C 12.1: 62 percent / Et3N; trimethylsilyl triflate / CH2Cl2 / 2 h / 0 °C 13.1: HCl / diethyl ether / 1 h / 20 °C 13.2: 98 percent / 4-(dimethylamino)pyridine; Et3N / diethyl ether / 10 h / 25 °C View Scheme