Multi-step reaction with 12 steps
1: 98 percent / pyridinium p-toluenesulfonate / CH2Cl2 / 2 h / Ambient temperature
2: 1.) n-butyl lithium / 1.) THF, hexane, -70 deg C, 3 h, 2.) THF, hexane, 0 deg C, 10 h
3: 1.) CuI / 1.) THF, -30 deg C, 2.) THF, -78 deg C, 1 h
4: 89 percent / LiAl(2)H4 / diethyl ether / 4 h / -10 °C
5: 71 percent / MnO2 / CH2Cl2 / 21 h / Ambient temperature
6: 87 percent / 9-borabicyclo<3.3.1>nonane, 1-(R)-α-pinene / tetrahydrofuran / 9 h / Ambient temperature
7: imidazole / CH2Cl2; dimethylformamide / 3 h / Ambient temperature
8: 0.1 N HCl / tetrahydrofuran / 9 h / Ambient temperature
9: 1.) oxalyl chloride, DMSO, 2.) triethylamine / 1.) CH2Cl2, -75 deg C, 20 min., 2.) CH2Cl2, -75 deg C, 1 h
10: 1.) nBuLi, 3.) nBuLi
11: 4-dimethylaminopyridine (DMAP) / CH2Cl2
12: tetra-n-butylammonium fluoride trihydrate / tetrahydrofuran / 0 °C
With
1H-imidazole; hydrogenchloride; dmap; manganese(IV) oxide; copper(l) iodide; 9-borabicyclo[3.3.1]nonane dimer; n-butyllithium; lithium aluminium deuteride; oxalyl dichloride; (+)-α-pinene; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; dimethyl sulfoxide; triethylamine;
In
tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide;