Multi-step reaction with 11 steps
1: 69 percent / benzene / Heating
2: 84 percent / K2CO3 / methanol / 0 deg C to RT
3: 92 percent / TsOH / diethyl ether / 0 deg C to RT
4: 83 percent / DIBAH / toluene / -65 °C
5: 98 percent / t-BuOOH, D-(-)-DIPT, Ti(O-iPr)4, 4 Angstroem molecular sieves / CH2Cl2 / -23 °C
6: 92 percent / Ti(O-iPr)4 / CH2Cl2 / 0 deg C to RT
7: 86 percent / Dowex (50W-X2) / methanol / Ambient temperature
8: 1.) t-BuOOH, D-(-)-DIPT, Ti(O-iPr)4, 4 Angstroem molecular sieves, 2.) CSA / 1.) CH2Cl2, -23 deg C, 2.) CH2Cl2, RT
9: p-TsOH / acetone / Ambient temperature
10: K2CO3 / ethanol / Ambient temperature
11: 100 percent / imidazole / dimethylformamide / Ambient temperature
With
1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; 4 A molecular sieve; Dowex (50W-X2); camphor-10-sulfonic acid; diisobutylaluminium hydride; potassium carbonate; D-(-)-diisopropyl tartrate; toluene-4-sulfonic acid;
In
methanol; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; benzene;
DOI:10.1016/0040-4039(95)02132-9