Multi-step reaction with 11 steps
1: 90 percent / NaH / dimethylformamide; tetrahydrofuran / 15 h / -3 °C
2: H2 / 10percent Pd-C / ethanol / 2.5 h / 760 Torr / Ambient temperature
3: Isobutyric acid / toluene / 65 h / Heating
4: 100 percent / LiAlH4 / tetrahydrofuran / 3 h / 0 °C
5: 89 percent / SO3*Py, DMSO, NEt3 / tetrahydrofuran / 0.25 h / Ambient temperature
6: 99.5 percent / CH2Cl2 / 48 h / Heating
7: 99 percent / H2 / 10percent Pd-C / ethanol / 0.5 h / 760 Torr / Ambient temperature
8: LiOH / methanol; tetrahydrofuran; H2O / 24 h / Ambient temperature
9: NEt3 / toluene / 1.) -10 deg C, 10 min, 2.) 0 deg C, 40 min
10: 1.) BuLi / 1.) THF, hexane, 15 min, -75 deg C, 2.) toluene, 1 h, -75 deg C
11: 1.) NaN(SiMe3)2, 2.) 2-benzenesulphonyl-3-phenyl-oxaziridine / 1.) THF, -78 deg C, 25 min, 2.) 20 min, -78 deg C
With
lithium hydroxide; lithium aluminium tetrahydride; n-butyllithium; pyridine-SO3 complex; hydrogen; sodium hexamethyldisilazane; sodium hydride; dimethyl sulfoxide; N-(benzenesulfonyl)-3-phenyloxaziridine; triethylamine;
palladium on activated charcoal; isobutyric Acid;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene;
DOI:10.1039/P19900000047