Multi-step reaction with 9 steps
1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / 6 h / Reflux
2.1: potassium carbonate / 5 h / 20 °C
3.1: triphenylphosphine; diethylazodicarboxylate / toluene / 6 h / -20 °C / Inert atmosphere
4.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; 2-hydroxyethanethiol / acetone / 3 h / 20 °C
5.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 6 h / 0 °C
6.1: titanium(IV) isopropylate; trimethylsilylazide / benzene / 2 h / 5 - 20 °C / Inert atmosphere
6.2: 1 h
7.1: triethylamine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere
8.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 0.75 h / -78 °C / Inert atmosphere
8.2: 0.5 h / -78 °C / Inert atmosphere
8.3: 0.5 h
9.1: pyridine; dihydrogen peroxide / dichloromethane / 0.5 h / 20 °C
With
pyridine; titanium(IV) isopropylate; trimethylsilylazide; dihydrogen peroxide; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; 2-hydroxyethanethiol; lithium diisopropyl amide; diethylazodicarboxylate;
In
tetrahydrofuran; hexane; dichloromethane; acetone; toluene; benzene;
3.1: Mitsunobu reaction;
DOI:10.1016/j.tet.2011.01.064