Multi-step reaction with 13 steps
1.1: borane-THF / tetrahydrofuran / 4 h / 0 - 20 °C
2.1: trifluoroacetic acid / dichloromethane / 4 h / 20 °C / Cooling with ice
3.1: potassium carbonate; copper(ll) sulfate pentahydrate; imidazole-1-sulfonyl azide hydrochloride / methanol / 20 °C / Cooling with ice
4.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C
4.2: 1 h / 20 °C
5.1: 0.17 h / 20 °C / Cooling with ice
6.1: diisobutylaluminium hydride / dichloromethane; hexane / 2.5 h / -78 °C
7.1: pyridine; Dess-Martin periodane / dichloromethane / 2 h / 0 - 20 °C
8.1: sodium hexamethyldisilazane / tetrahydrofuran; benzene / 1.75 h / -78 - 20 °C
9.1: triphenylphosphine; water / benzene / 3 h / 20 - 55 °C
10.1: N-ethyl-N,N-diisopropylamine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / acetonitrile / 2.5 h / 0 - 20 °C
11.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2.5 h / 0 - 20 °C
12.1: triethylamine / dichloromethane / 0.17 h / 0 °C
13.1: tetrahydrofuran; 1,2-dichloro-ethane / 0.17 h / 0 °C
With
pyridine; imidazole-1-sulfonyl azide hydrochloride; copper(ll) sulfate pentahydrate; borane-THF; oxalyl dichloride; tetrabutyl ammonium fluoride; water; sodium hexamethyldisilazane; diisobutylaluminium hydride; potassium carbonate; Dess-Martin periodane; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; trifluoroacetic acid;
In
tetrahydrofuran; methanol; hexane; dichloromethane; 1,2-dichloro-ethane; acetonitrile; benzene;
4.1: |Swern Oxidation / 4.2: |Swern Oxidation;
DOI:10.1021/jm401370h