Multi-step reaction with 11 steps
1: sodium chlorite; sodium phosphate monobasic monohydrate / 2-methyl-but-2-ene; water; tert-butyl alcohol / 0 °C
2: sulfuric acid / 0 - 20 °C / Inert atmosphere
3: toluene-4-sulfonic acid / tetrahydrofuran / 80 °C / Inert atmosphere
4: chloro-trimethyl-silane; sodium cyanoborohydride / acetonitrile / 0 °C / Inert atmosphere; Heating
5: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / ethyl acetate / 3 h / 80 °C / Inert atmosphere
6: magnesium iodide / dichloromethane / -78 - -20 °C / Inert atmosphere
7: boron trichloride / dichloromethane / 1 h / -78 °C / Inert atmosphere
8: 10-camphorsufonic acid / dichloromethane / 1 h / 40 °C / Inert atmosphere; Sonication
9: potassium phosphate / dimethyl sulfoxide / 50 °C / Inert atmosphere
10: lithium hydroxide monohydrate; water / 1,4-dioxane / 75 °C / Inert atmosphere
11: pyridine; 1,3,5-trichloro-2,4,6-triazine / 1,2-dichloro-ethane / 1.08 h / 20 - 75 °C / Inert atmosphere
With
pyridine; sodium chlorite; potassium phosphate; chloro-trimethyl-silane; 1,3,5-trichloro-2,4,6-triazine; sodium phosphate monobasic monohydrate; lithium hydroxide monohydrate; sulfuric acid; 10-camphorsufonic acid; water; boron trichloride; sodium cyanoborohydride; toluene-4-sulfonic acid; magnesium iodide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione;
In
tetrahydrofuran; 1,4-dioxane; 2-methyl-but-2-ene; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; 1,2-dichloro-ethane; acetonitrile; tert-butyl alcohol;
1: Pinnick oxidation / 6: intramolecular halo-Michael aldol reaction;
DOI:10.1021/ja203642n