Multi-step reaction with 9 steps
1: pertrifluoroacetic acid, Na2HPO4 / CH2Cl2
2: 10 percent / aq. KMnO4 / acetone / 3 h
3: 1.) triethylamine, diphenylphosphoryl azide, 2.) water / 1.) benzene, reflux, 1 h, 2.) reflux, 30 min
4: 1.) acetic anhydride, 2.) methanolic K2CO3 / 1.) 120 - 125 deg C, 2 h, 2.) room temperature, 21 h
5: 88 percent / activated manganese oxide / CHCl3 / 2 h
6: 1.) n-butyllithium, HMPA / 1.) THF, -78 - -75 deg C, 2.) THF, -75 -> 15 deg C, 40 min
7: activated manganese dioxide / CHCl3 / 1 h
8: 1.) KH / 1.) benzene, room temperature, 15 min, 2.) benzene, room temperature, 75 min
9: 60 percent / aq. sodium hydrosulfite / methanol / 3 h / Heating
With
N,N,N,N,N,N-hexamethylphosphoric triamide; manganese oxide; manganese(IV) oxide; potassium permanganate; sodium disulfite; disodium hydrogenphosphate; n-butyllithium; diphenylphosphoranyl azide; water; acetic anhydride; potassium hydride; potassium carbonate; triethylamine; trifluoroacetic acid;
In
methanol; dichloromethane; chloroform; acetone;
DOI:10.1021/ja00366a028