Multi-step reaction with 9 steps
1: 93 percent / i-Pr2NH, 4-dimethylaminopyridine / CH2Cl2 / 16 h / Ambient temperature
2: 1) O3, pyridine, 2) NaBH4 / 1) MeOH, CH2Cl2, -78 deg C, 30 min, 2) rt, 4 h
3: 90 percent / pyridine / 72 h / 4 °C
4: 95 percent / dimethylsulfoxide / 4 h / 90 °C
6: 1) NaH / 1) DMF, hexane, 1 h, rt, 2) 24 h
7: 97 percent / AG 50W-X4 / methanol / 96 h
8: 98 percent / pyridinium dichromate, pyridinium tosylate / CH2Cl2 / 12 h
9: 1) n-BuLi / 1) THF, hexane, -78 deg C, 30 min, 2) THF, a) -78 deg C, 1 h, b) rt, 3 h
With
pyridine; dmap; sodium tetrahydroborate; dipyridinium dichromate; n-butyllithium; AG 50W-X4; pyridinium p-toluenesulfonate; sodium hydride; ozone; diisopropylamine;
In
methanol; dichloromethane; dimethyl sulfoxide;
DOI:10.1016/S0040-4020(01)86275-X