Multi-step reaction with 9 steps
1: 58 percent / Hg(OAc)2 / 16 h / Heating
2: 32 percent / xylene / 20 h / Heating
3: 85 percent / NaBH4 / ethanol / 0.5 h / 40 °C
4: Et3N / CH2Cl2 / 1 h / 0 °C
5: LiBr / acetone / 1 h / Heating
6: 35 percent / K2CO3, KOH, 18-crown-6 / dioxane / 18 h / Heating
7: 1.) ascorbinic acid, 2.) Et3N / 1.) dioxane, H2O, 40 deg C, 15 min, 2.) CHCl3, 0 deg C, 1 h
8: 56 percent / NBS, benzoylperoxide / CCl4 / 14 h / Heating; var. reag.: 1,3-dibromo-5,5-dimethylhydantoine
9: 28 percent / NaOMe / methanol; tetrahydrofuran / 0.5 h / Ambient temperature; spontaneous oxidation
With
potassium hydroxide; sodium tetrahydroborate; N-Bromosuccinimide; Perbenzoic acid; 18-crown-6 ether; mercury(II) diacetate; sodium methylate; potassium carbonate; triethylamine; lithium bromide; ascorbic acid;
In
tetrahydrofuran; 1,4-dioxane; methanol; tetrachloromethane; ethanol; dichloromethane; acetone; xylene;
DOI:10.1055/s-1994-25641