Multi-step reaction with 13 steps
1: 100 percent / imidazole / dimethylformamide / 3.5 h / Ambient temperature
2: 1.) O3; 2.) Ph3P / 1.) CH2Cl2, -78 deg C; 2.) CH2Cl2, -78 deg C to RT
3: benzene / 12 h / 80 °C
4: 95 percent / 1.0 M di-isobutylaluminum hydride / CH2Cl2; hexane / 1 h / -78 °C
5: 93 percent / (+)-DET, Ti(O-iPr)2, 3.0 M t-BuOOH, 4 Angstroem molecular sieves / CH2Cl2; 2,2,4-trimethyl-pentane / 70 h / -20 °C
6: 100 percent / SO3*py complex, Et3N / dimethylsulfoxide; CH2Cl2 / 3 h / Ambient temperature
7: 94 percent / 1.0 M NaHMDS / tetrahydrofuran / 1 h / 0 °C
8: 97 percent / 1.0 M TBAF / tetrahydrofuran / 0.25 h / 0 °C
9: 53 percent / camphorsulfonic acid / CH2Cl2 / 1 h / 0 °C
10: 97 percent / pyridine, 4-dimethylaminopyridine / CH2Cl2 / 13 h / Ambient temperature
11: 1.) O3; 2.) PPh3 / 1.) CH2Cl2, -78 deg C; 2.) CH2Cl2, -78 deg C to RT
12: benzene / 6.5 h / 80 °C
13: 10 percent / H2 / Pd(OH)2-C / methanol / 20 h / Ambient temperature
With
pyridine; 1H-imidazole; tert.-butylhydroperoxide; dmap; diisobutylaluminum hydride; pyridine-SO3 complex; diethyl (2R,3R)-tartrate; titanium(II) diisopropoxide; 4 A molecular sieve; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; sodium hexamethyldisilazane; ozone; triethylamine; triphenylphosphine;
palladium hydroxide - carbon;
In
tetrahydrofuran; methanol; 2,2,4-trimethylpentane; hexane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; benzene;