Multi-step reaction with 10 steps
1: 80 percent / SnCl4 / diethyl ether / -85 °C
2: imidazole / dimethylformamide / 10 h / Ambient temperature
3: 68 percent / KMnO4, cis-dicyclohexano-18-crown-6 ether / CH2Cl2 / 2 h / Ambient temperature
4: 1.) 1 M aq. LiOH, 2.) SiO2, O.65 M aq. NaIO4 / 1.) THF, 0 deg C, 1 h, 2.) CH2Cl2, RT, 2 h
5: NaBH4 / ethanol / 4 h / Ambient temperature
6: 88 percent / imidazole / dimethylformamide / 4 h / Ambient temperature
7: 95 percent / 70percent aq. AcOH / tetrahydrofuran / 24 h / 50 °C
8: SiO2, 0.65 M aq. NaIO4 / CH2Cl2 / 0.5 h
9: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 2 h, 2.) THF, hexane, 20 deg C, 1 d
10: phenyl disulfide / cyclohexane / 12 h / Irradiation
With
1H-imidazole; lithium hydroxide; sodium tetrahydroborate; potassium permanganate; sodium periodate; n-butyllithium; dicyclohexano-18-crown-6; silica gel; tin(IV) chloride; acetic acid; diphenyldisulfane;
In
tetrahydrofuran; diethyl ether; ethanol; dichloromethane; cyclohexane; N,N-dimethyl-formamide;
DOI:10.1016/S0957-4166(97)00431-X