Multi-step reaction with 12 steps
1: 10 g / baker's yeast, sucrose / H2O; ethanol / 30 °C
2: 4-N,N-dimethylaminopyridine / pyridine / Ambient temperature
3: 95 percent / LiAlH4 / tetrahydrofuran / 1 h / 0 °C
4: 87 percent / p-TsOH / CH2Cl2 / 3 h / Ambient temperature
5: 83 percent / NBS / AIBN / benzene / 1 h / 50 °C
6: 83 percent / LiAlH4 / tetrahydrofuran / Ambient temperature
7: 99 percent / Amberlite IR-120 / H2O / 3 h / Heating
8: 90 percent / p-TsOH / CH2Cl2 / Ambient temperature
9: 60percent NaH / tetrahydrofuran / 1 h / Ambient temperature
10: LDA / tetrahydrofuran; hexamethylphosphoric acid triamide / 1 h / 0 °C
11: 1.) p-TsCl / 1.) pyridine, 0 deg C, 3 h, 2.) pyridine, room temp.
12: t-BuOK / 2-methyl-propan-2-ol / 2 h / Ambient temperature
With
N-Bromosuccinimide; lithium aluminium tetrahydride; baker's yeast; Amberlite IR-120; potassium tert-butylate; sodium hydride; p-toluenesulfonyl chloride; lithium diisopropyl amide; Sucrose;
dmap; 2,2'-azobis(isobutyronitrile); toluene-4-sulfonic acid;
In
tetrahydrofuran; pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; ethanol; dichloromethane; water; tert-butyl alcohol; benzene;
DOI:10.1016/S0040-4020(01)86136-6