Multi-step reaction with 11 steps
1: dmap / benzene / 17 h / 20 °C / Inert atmosphere
2: pyridinium p-toluenesulfonate / methanol / 0.75 h / 20 °C / Inert atmosphere
3: 4-methylmorpholine N-oxide; tetrapropylammonium perruthennate / dichloromethane / 0.75 h / 20 °C / Molecular sieve; Inert atmosphere
4: sodium chlorite; sodium dihydrogen phosphate; 2-methyl-but-2-ene / water; tert-butyl alcohol / 17 h / 20 °C
5: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 18 h / 20 °C
6: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 1.17 h / 20 °C
7: 4-methylmorpholine N-oxide; tetrapropylammonium perruthennate / dichloromethane / 2.5 h / 20 °C / Molecular sieve
8: tetrakis(triphenylphosphine) palladium(0); phenylsilane / dichloromethane / 6 h / 20 °C
9: triethylamine; dmap; 2-methyl-6-nitrobenzoic anhydride / dichloromethane / 20.5 h / 20 °C
10: tetrakis(triphenylphosphine) palladium(0); phenylsilane / dichloromethane / 3.67 h / 20 °C
11: pyridine hydrogenfluoride; pyridine / tetrahydrofuran / 2 h / 20 °C
With
pyridine; dmap; sodium chlorite; tetrakis(triphenylphosphine) palladium(0); tetrapropylammonium perruthennate; sodium dihydrogen phosphate; 2-methyl-but-2-ene; phenylsilane; 2-methyl-6-nitrobenzoic anhydride; pyridinium p-toluenesulfonate; pyridine hydrogenfluoride; 4-methylmorpholine N-oxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone;
In
tetrahydrofuran; methanol; dichloromethane; water; tert-butyl alcohol; benzene;
DOI:10.1021/acs.orglett.6b01235