Multi-step reaction with 17 steps
1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 0 - 20 °C
2: 1H-imidazole / N,N-dimethyl-formamide / 5.5 h / 20 °C
3: sodium hydroxide / tetrahydrofuran; methanol / 20 °C
4: N-ethyl-N,N-diisopropylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / chloroform / 20 °C
5: sodium hydroxide / tetrahydrofuran; methanol / 20 - 75 °C
6: toluene / 120 °C
7: diisobutylaluminium hydride / tetrahydrofuran / -78 - 0 °C
8: n-butyllithium / tetrahydrofuran / -78 - 0 °C
9: sodium hydrogencarbonate; Dess-Martin periodane / chloroform
10: sodium carbonate / ethanol / 1.5 h / 80 °C
11: Iodine monochloride / dichloromethane / 2 h / 0 - 20 °C
12: potassium phosphate / bis-triphenylphosphine-palladium(II) chloride / N,N-dimethyl-formamide; water / 80 °C
13: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran / 0.67 h / 0 - 70 °C
14: sodium hypochlorite; sodium chlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / acetonitrile; water / 1.67 h / 20 °C / Phosphate buffer
15: potassium carbonate / N,N-dimethyl-formamide / 1.33 h / 20 °C
16: trifluoroacetic acid / chloroform / 2.67 h / 20 - 50 °C
17: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 20 °C
With
1H-imidazole; sodium hypochlorite; sodium chlorite; potassium phosphate; n-butyllithium; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; tetrabutyl ammonium fluoride; Iodine monochloride; diisobutylaluminium hydride; sodium hydrogencarbonate; sodium carbonate; potassium carbonate; benzotriazol-1-ol; Dess-Martin periodane; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; 9-bora-bicyclo[3.3.1]nonane; trifluoroacetic acid; sodium hydroxide;
bis-triphenylphosphine-palladium(II) chloride;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; chloroform; water; N,N-dimethyl-formamide; toluene; acetonitrile;