Multi-step reaction with 14 steps
1: 98 percent / imidazole / dimethylformamide / 23 °C
2: 94 percent / DIBAL-H / diethyl ether / -50 - -30 °C
3: 86 percent / MnO2 / CH2Cl2 / 23 °C
4: 90 percent / CH2Cl2 / Heating
5: 96 percent / DIBAL-H / diethyl ether / -50 °C
6: 98 percent / MnO2 / CH2Cl2 / 23 °C
7: 89 percent / LiN(TMS)2 / tetrahydrofuran / 0 °C
8: 73 percent / BHT / trichloroethene / 16 h / 135 °C
9: 97 percent / DIBAL-H / CH2Cl2 / -78 - -30 °C
10: 89 percent / imidazole / dimethylformamide / 23 °C
11: 1) DMSO, (COCl)2, 2) Et3N / 1) -78 deg C, CH2Cl2
12: K2CO3 / 0 °C
13: DMAP, Et3N / CH2Cl2
14: 1) LiN(TMS)2 / 1) THF-HMPA, -78 to 23 deg C, 1 h
With
1H-imidazole; dmap; manganese(IV) oxide; oxalyl dichloride; 2,6-di-tert-butyl-4-methyl-phenol; diisobutylaluminium hydride; potassium carbonate; dimethyl sulfoxide; triethylamine; lithium hexamethyldisilazane;
In
tetrahydrofuran; diethyl ether; dichloromethane; Trichloroethylene; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(00)70684-8