Multi-step reaction with 10 steps
1: DIBALH / toluene / 0.5 h / -78 °C
2: NaBH4 / methanol / 0.5 h / 0 °C
3: 96 percent / Et3N / CH2Cl2 / 2 h / Ambient temperature
4: 1.) n-BuLi / 1.) HMPA, THF, -20 deg C, 2 h; 2.) HMPA, THF, -20 deg C, 2 h
5: IBX / dimethylsulfoxide; tetrahydrofuran / 5 h / Ambient temperature
6: tetrahydrofuran; diethyl ether / 1 h / Ambient temperature
7: 64 percent / BCl3, 1,3-propanedithiol / CH2Cl2 / 1 h / Ambient temperature
8: 63 percent / PPTS / CH2Cl2 / 48 h / Ambient temperature
9: 98 percent / 2,6-lutidine / CH2Cl2 / 1 h / Ambient temperature
10: 1.) n-BuLi / 1.) HMPA, THF, -20 deg C, 1 h; 2.) HMPA, THF, -20 deg C, 0.5 h
With
2,6-dimethylpyridine; 1.3-propanedithiol; sodium tetrahydroborate; n-butyllithium; pyridinium p-toluenesulfonate; boron trichloride; diisobutylaluminium hydride; triethylamine; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; dimethyl sulfoxide; toluene;
DOI:10.1016/S0040-4039(98)00619-4