Multi-step reaction with 16 steps
1.1: sodium hydride / N,N-dimethyl-formamide / 1.17 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; methanol / 18 h / 0 - 20 °C
6.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.75 h / -78 °C
7.1: n-butyllithium / tetrahydrofuran / 2 h / 0 °C
7.2: 16.33 h / -78 - 20 °C
8.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 24 h / 20 °C
8.2: 4 h / 50 °C
9.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.75 h / -78 °C
9.2: 0.5 h
10.1: triphenylphosphine / dichloromethane / 0.5 h / 0 °C
10.2: 2 h / -78 °C
11.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone; water / dichloromethane / 6 h / 20 °C
12.1: tetrahydrofuran; hexanes / 0.5 h / -78 °C
13.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 4 h / 0 - 20 °C
14.1: sulfuric acid / 0.25 h / 20 °C
15.1: N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate / acetonitrile / 2 h / Cooling with ice; Reflux
16.1: ammonia / methanol / 16 h / 20 °C
With
sodium periodate; n-butyllithium; N,O-bis-(trimethylsilyl)-acetamide; oxalyl dichloride; trimethylsilyl trifluoromethanesulfonate; sulfuric acid; ammonia; water; sodium hydride; acetic acid; dimethyl sulfoxide; triethylamine; 9-bora-bicyclo[3.3.1]nonane; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium hydroxide;
In
tetrahydrofuran; 1,4-dioxane; methanol; hexanes; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; mineral oil;
15.1: Vorbrugen reaction;