Multi-step reaction with 18 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: triethylamine / dmap / dichloromethane / 2.5 h / 0 °C
9.1: sulfuric acid / 16 h / 20 °C
10.1: N,O-bis-(trimethylsilyl)-acetamide / acetonitrile / Heating
10.2: Cooling with ice; Reflux
11.1: ammonia / methanol
13.1: pyridine / 16 h / 0 - 20 °C
14.1: potassium thioacetate / N,N-dimethyl-formamide / 20 °C
14.2: 2 h
15.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone; water / dichloromethane / 3 h
16.1: triethylamine; triethylamine tris(hydrogen fluoride) / tetrahydrofuran / 16 h / 20 °C
17.1: pyridine / 16 h / 0 - 20 °C
18.1: 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; ammonia; water; sodium hydride; acetic acid; dimethyl sulfoxide; triethylamine tris(hydrogen fluoride); triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium hydroxide; potassium thioacetate;
dmap; sulfuric acid;
In
tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; mineral oil;