Multi-step reaction with 11 steps
1.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran; toluene / 24 h / 20 °C
2.1: sodium tetrahydroborate; ethanol / 20 °C
3.1: pyridine; phosphorus tribromide / diethyl ether / 3 h / 20 °C
4.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / Cooling with acetone-dry ice
4.2: 20 °C / Cooling with acetone-dry ice
5.1: lithium borohydride; water / diethyl ether / 0.67 h / 0 °C
6.1: 1H-imidazole; iodine; triphenylphosphine / dichloromethane / 3 h
7.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.25 h / Cooling with acetone-dry ice
7.2: 20 °C / Cooling with acetone-dry ice
8.1: water; citric acid / tetrahydrofuran
9.1: dichloromethane
10.1: diisobutylaluminium hydride / tetrahydrofuran; hexane / -78 - 20 °C
10.2: 1 h
11.1: sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine / 1 h / 0 - 20 °C
With
pyridine; 1H-imidazole; sodium tetrahydroborate; lithium borohydride; ethanol; di-isopropyl azodicarboxylate; water; iodine; sulfur trioxide pyridine complex; phosphorus tribromide; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; triphenylphosphine; citric acid; lithium hexamethyldisilazane;
In
tetrahydrofuran; diethyl ether; hexane; dichloromethane; toluene;