Multi-step reaction with 10 steps
1: 65 percent / NBS, AIBN / CCl4 / 8 h / Irradiation
2: 100 percent / benzene / 26 h / Ambient temperature
3: 60 percent / Na2CO3 / H2O; CHCl3 / 1 h / Ambient temperature
4: 90 percent / (DHQ)2PHAL, K2CO3, K3Fe(CN)6, OsO4 / 2-methyl-propan-2-ol; H2O / 8 h / 0 °C
5: 95 percent / imidazole / CH2Cl2 / 1 h / 0 °C
6: 90 percent / PPh3, DEAD / tetrahydrofuran / 6 h / 0 °C
7: 93 percent / 1N HCl / methanol / 1 h / Ambient temperature
8: 85 percent / 2,6-lutidine / CH2Cl2 / 2 h / 80 °C
9: 90 percent / 1.) conc. HCl, 2.) NaHCO3 / H2O / 12 h / 100 °C
10: 60 percent / EDC, HOBt / dimethylformamide / 8 h / Ambient temperature
With
1H-imidazole; 2,6-dimethylpyridine; hydrogenchloride; N-Bromosuccinimide; osmium(VIII) oxide; Hydroquinone 1,4-phthalazinediyl diether; 2,2'-azobis(isobutyronitrile); sodium hydrogencarbonate; sodium carbonate; potassium carbonate; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triphenylphosphine; potassium hexacyanoferrate(III); diethylazodicarboxylate;
In
tetrahydrofuran; methanol; tetrachloromethane; dichloromethane; chloroform; water; N,N-dimethyl-formamide; tert-butyl alcohol; benzene;
DOI:10.1016/S0040-4039(97)01749-8