Multi-step reaction with 10 steps
1: 1.) NaCl, 2.) LiAlH4 / 1.) DMSO, H2O, 160-170 deg C, 4 h, 2.) THF, 0 deg C
2: triethylamine / CH2Cl2 / 3 h / 0 °C
3: 77 percent / dimethylformamide / 60 °C
4: 1.) 1 M Dibal 2.) 5percent aq. HCl / 1.) CH2Cl2, hexane, 0 deg C, 1 h, 2.) 30 min
5: LiAlH4 / tetrahydrofuran / 30 h / 0 °C
6: triethylamine / CH2Cl2 / 3 h / 0 °C
7: NaI / acetone / 2 h / Heating
8: 1.) NaH / 1.) DMF, RT, 30 min, 2.) DMF, THF, 50 deg C, 5 h
9: 100 percent / NBS, benzoyl peroxide / CCl4 / 0.25 h / Heating; Irradiation
10: tert-BuOK / tetrahydrofuran; 2-methyl-propan-2-ol / 1 h / Ambient temperature
With
hydrogenchloride; N-Bromosuccinimide; lithium aluminium tetrahydride; Perbenzoic acid; potassium tert-butylate; sodium hydride; diisobutylaluminium hydride; triethylamine; sodium iodide; sodium chloride;
In
tetrahydrofuran; tetrachloromethane; dichloromethane; N,N-dimethyl-formamide; acetone; tert-butyl alcohol;
DOI:10.1021/jo00244a015