Multi-step reaction with 18 steps
1: triethylamine / CH2Cl2
2: conc. sulfuric acid / diethyl ether / 3 h
3: 1.) N-methylmorpholine N-oxide, osmium tetraoxide, 2.) sodium periodate / 1.) THF, H2O, overnight, 2.)ethanol, H2O, 2 h
4: sodium chlorite, sodium dihydrogen phosphate monohydrate / tetrahydrofuran; 2-methyl-propan-2-ol; various solvent(s); H2O / 0.5 h
5: 1-hydroxybenzotriazole, triethylamine, 1-<3-(dimethylamino)propyl>-3-ethylcarbodimide / dimethylformamide
6: nitromethane, aluminum chloride / benzene / 1 h
7: 48 percent / methanol; diethyl ether
8: 1-<3-(dimethylamino)propyl>-3-ethylcarbodimide, dichloroacetic acid / dimethylsulfoxide; toluene / 2 h / Ambient temperature
9: lithium hydroxide / tetrahydrofuran; methanol; H2O / 1 h
10: oxalyl chloride, N,N-dimethylformamide / CH2Cl2 / 1 h
11: triethylamine / CH2Cl2
12: 90 percent / conc. sulfuric acid / diethyl ether / 3 h
13: 1.) N-methylmorpholine N-oxide, osmium tetraoxide, 2.) sodium periodate / 1.) THF, H2O, overnight, 2.) ethanol, H2O, 2 h
14: sodium chlorite, sodium dihydrogen phosphate monohydrate / tetrahydrofuran; 2-methyl-propan-2-ol; various solvent(s); H2O / 0.5 h
15: 73 percent / 1-hydroxybenzotriazole, triethylamine, 1-<3-(dimethylamino)propyl>-3-ethylcarbodimide / dimethylformamide
16: 83 percent / nitromethane, aluminum chloride / benzene / 1 h
17: 32 percent / sodium hypophosphite monohydrate, pyridine, acetic acid / Raney nickel / H2O / 2 h / 60 °C
18: 1-<3-(dimethylamino)propyl>-3-ethylcarbodimide, dichloroacetic acid / dimethylsulfoxide; toluene / 2 h / Ambient temperature
With
pyridine; dichloro-acetic acid; lithium hydroxide; sodium chlorite; sodium periodate; sodium dihydrogenphosphate; osmium(VIII) oxide; sodium hypophosphite; aluminium trichloride; oxalyl dichloride; nitromethane; sulfuric acid; benzotriazol-1-ol; acetic acid; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; 4-methylmorpholine N-oxide; triethylamine; N,N-dimethyl-formamide;
nickel;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; benzene;
DOI:10.1021/jm00001a014