Multi-step reaction with 12 steps
1: 95 percent / DIBAL / CH2Cl2 / 0.25 h / -78 °C
2: 84 percent / MnO2 / CH2Cl2 / 18 h / Ambient temperature
3: 84 percent / tetrahydrofuran / 0.17 h / -25 °C
4: 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C
5: 96 percent / K2CO3, methanol / tetrahydrofuran / 1 h
6: 90 percent / pyridine / CH2Cl2 / 0.5 h / 0 °C
7: 98 percent / Et3N, Pd(OAc)2, 1,3-bis(diphenylphosphino)propane / dimethylsulfoxide / 1 h / 75 °C
8: 100 percent / DIBAL / CH2Cl2 / 0.33 h / -78 °C
9: 91 percent / CBr4, Ph3P / CH2Cl2 / 1 h
10: 95 percent / K2CO3 / dimethylformamide / 0.5 h
11: TBAF / tetrahydrofuran / 48 h / Ambient temperature
12: 72 percent / 80percent MCPBA / CH2Cl2 / 0.5 h / 0 °C
With
pyridine; 2,6-dimethylpyridine; methanol; manganese(IV) oxide; palladium diacetate; carbon tetrabromide; 1,3-bis-(diphenylphosphino)propane; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; potassium carbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine;
In
tetrahydrofuran; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;
DOI:10.1021/jm00074a012