Multi-step reaction with 12 steps
1.1: trimethylsilyl trifluoromethanesulfonate / diethyl ether / 1 h / -78 °C / Inert atmosphere
2.1: water; toluene-4-sulfonic acid / methanol; benzene / 5 h / 20 °C / Inert atmosphere
3.1: triethylamine / dichloromethane / 12 h / 20 °C / Inert atmosphere
4.1: cerium(III) chloride / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere
4.2: -78 - 20 °C / Inert atmosphere
4.3: -78 - 20 °C
5.1: trimethylsilyl trifluoromethanesulfonate / diethyl ether / 1 h / -78 °C / Inert atmosphere
6.1: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran; N,N-dimethyl-formamide / 21 h / 20 °C / Inert atmosphere
7.1: dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine / dichloromethane / 0.08 h / 0 °C / Inert atmosphere
7.2: 1.25 h / 0 °C / Inert atmosphere
8.1: sodium chlorite; potassium dihydrogenphosphate / 2-methyl-but-2-ene; water; tert-butyl alcohol / -10 - 20 °C
9.1: pyridine; pyridine hydrogenfluoride / tetrahydrofuran / 48 h / Inert atmosphere
10.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 0 - 20 °C / Inert atmosphere
10.2: 14 h / 40 °C / Inert atmosphere
11.1: cerium(III) chloride heptahydrate / methanol / -42 - 20 °C / Inert atmosphere
11.2: 1 h / -42 °C / Inert atmosphere
12.1: pyridine; dmap / dichloromethane / 36 h / 20 °C / Inert atmosphere
With
pyridine; dmap; sodium chlorite; potassium dihydrogenphosphate; cerium(III) chloride; trimethylsilyl trifluoromethanesulfonate; cerium(III) chloride heptahydrate; 2,4,6-trichlorobenzoyl chloride; tetrabutyl ammonium fluoride; water; toluene-4-sulfonic acid; pyridine hydrogenfluoride; acetic acid; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine;
In
tetrahydrofuran; methanol; 2-methyl-but-2-ene; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol; benzene;