Multi-step reaction with 13 steps
2: 92 percent / diisobutyl aluminum hydride / CH2Cl2; hexane / 1 h / -78 °C
3: 90 percent / (-)-diisopropyl tartrate, titanium tetraisopropoxide, t-butyl hydroperoxide, MS 4 Angstroem / CH2Cl2; toluene / 11 h / -20 °C
4: 91 percent / Red-al / toluene; tetrahydrofuran / 10.2 h / 0 °C
5: 93 percent / triethylamine, 4-DMAP / CH2Cl2 / 4 h / Ambient temperature
6: sodium hydride / tetrahydrofuran; dimethylformamide / 5 h / Ambient temperature
7: sodium bromide / dimethylformamide / 48 h / Ambient temperature
8: Mg / tetrahydrofuran / 1 h / Irradiation
9: CuI / tetrahydrofuran
10: 93 percent / 4-dimethylaminopyridine / tetrahydrofuran / 12 h / Ambient temperature
11: 62 percent / lithium aluminum hydride / tetrahydrofuran / 14 h / Ambient temperature
12: 91 percent / 4-dimethylaminopyridine / CH2Cl2 / 12 h / Ambient temperature
13: 86 percent / PPTS / methanol / 36 h / Ambient temperature
With
titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; lithium aluminium tetrahydride; (-)-diisopropyl tartrate; MS 4 Angstroem; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; magnesium; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; sodium bromide;
copper(l) iodide;
In
tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1016/S0040-4020(01)81547-7