Multi-step reaction with 17 steps
1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / Cooling with ice
2.1: water; acetic acid / 16 h / 20 °C
3.1: sodium periodate / 1,4-dioxane; water / 1.67 h
4.1: sodium hydroxide; water / tetrahydrofuran / 72 h / 20 °C / Cooling with ice
5.1: triethylamine / dichloromethane / 16 h / 0 - 20 °C
6.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.75 h / -78 °C
6.2: 1 h / -78 - 20 °C
7.1: cerium(III) chloride / tetrahydrofuran / 1.58 h / 0 °C
7.2: 3 h / -78 °C
7.3: 20 °C
8.1: sulfuric acid / 2 h / 20 °C
9.1: N,O-bis-(trimethylsilyl)-acetamide / acetonitrile / 1.5 h / 55 °C
9.2: 0 - 60 °C
10.1: potassium carbonate / methanol / 96 h / 20 °C
10.2: 12 h / 0 °C
11.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 2 h / 20 °C
11.2: 1.5 h
12.1: pyridine / 5.5 h / 0 - 20 °C
13.1: potassium thioacetate / N,N-dimethyl-formamide / 4 h / 20 °C
13.2: 12 h
14.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone; water / dichloromethane / 3.5 h
15.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 18 h
16.1: pyridine / 6.5 h / 0 - 20 °C
17.1: 1H-tetrazole; 1-methyl-1H-imidazole / N,N-dimethyl-formamide / 5 h / 20 °C
With
pyridine; 1-methyl-1H-imidazole; 1H-tetrazole; sodium periodate; N,O-bis-(trimethylsilyl)-acetamide; cerium(III) chloride; oxalyl dichloride; tetrabutyl ammonium fluoride; water; sodium hydride; potassium carbonate; acetic acid; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium hydroxide; potassium thioacetate;
sulfuric acid;
In
tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; mineral oil;