Multi-step reaction with 15 steps
1: 79 percent / NaH / dimethylformamide / 2 h
2: 66 percent / decahydronaphthalene / 7 h / 200 °C
3: 83 percent / PhI(OAc)2 / 12 h
4: 70 percent / Zn; AcOH / 7 h
5: 92 percent / K2CO3 / dimethylformamide / 12 h
6: 97 percent / TsOH*H2O; 4 Angstroem molecular sieves / methanol / 12 h / Heating
7: 95 percent / OsO4; aq. NaIO4 / CCl4; 2-methyl-propan-2-ol / 1.5 h
8: 95 percent / NaBH4 / methanol / 1.5 h / 0 °C
9: 92 percent / NaH / tetrahydrofuran / 12 h
10: 95 percent / Amberlite IR-120 / acetone; H2O / 12 h
11: 66 percent / CuI / Pd(PPh3)4 / toluene / 40 h / Heating
12: 78 percent / Bu2BOSO2CF3
13: 95 percent / 2,6-lutidine / CH2Cl2 / 1 h
14: 89 percent / tetrahydrofuran / 6 h / 0 °C
15: 89 percent / DIBALH / CH2Cl2 / 1 h / 0 °C
With
2,6-dimethylpyridine; sodium tetrahydroborate; sodium periodate; copper(l) iodide; osmium(VIII) oxide; Amberlite IR-120; [bis(acetoxy)iodo]benzene; 4 A molecular sieve; di-n-butylboryl trifluoromethanesulfonate; sodium hydride; diisobutylaluminium hydride; potassium carbonate; toluene-4-sulfonic acid; acetic acid; zinc;
tetrakis(triphenylphosphine) palladium(0);
In
tetrahydrofuran; methanol; tetrachloromethane; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; decalin; tert-butyl alcohol;
2: Claisen rearrangement / 11: Stille coupling;
DOI:10.1039/b205487f