Multi-step reaction with 8 steps
1: 90 percent / LAH / tetrahydrofuran / 1 h / 0 °C
2: 90 percent / KOH / dioxane / 3 h / Heating
3: 97 percent / magnesium monoperoxyphthalate (MMPP) / methanol / 0 °C
4: 90 percent / n-BuLi, TMEDA / toluene; CH2Cl2 / 0.25 h / -78 °C
5: 88 percent / p-TsOH, 3A MS / CH2Cl2 / 36 h / Heating
6: 75 percent / Na(Hg), Na2HPO4, MeOH / 4 h / -20 deg C to r.t.
7: 95 percent / OsO4, Me3NO / acetone; H2O / Ambient temperature
8: 90 percent / BF3*OEt, EtSH / Ambient temperature
With
methanol; potassium hydroxide; disodium hydrogenphosphate; osmium(VIII) oxide; lithium aluminium tetrahydride; n-butyllithium; sodium amalgam; N,N,N,N,-tetramethylethylenediamine; trimethylamine-N-oxide; boron trifluoride diethyl etherate; toluene-4-sulfonic acid; magnesium monoperoxyphthalate hexahydrate; ethanethiol;
In
tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; acetone; toluene;
DOI:10.1021/jo00033a002