Multi-step reaction with 7 steps
1.1: N,N,N',N'-tetramethylguanidine / N,N-dimethyl-formamide / 0.5 h / 20 °C / Inert atmosphere
1.2: 5 h / 100 °C / Inert atmosphere
2.1: trifluoroacetic acid / water / 10 h / 20 °C / Inert atmosphere
2.2: 4 h / 0 - 20 °C / Inert atmosphere
3.1: p-toluenesulfonyl chloride; pyridine / toluene / 72.5 h / 0 - 4 °C / Inert atmosphere
4.1: sodium periodate / methanol; water / 5 h / 20 °C / Inert atmosphere
5.1: pyridine / 24.5 h / 0 - 4 °C / Inert atmosphere
6.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 3 h / 20 °C / Inert atmosphere
7.1: methanol / 48 h / 20 °C / Inert atmosphere
With
pyridine; sodium periodate; 1,8-diazabicyclo[5.4.0]undec-7-ene; p-toluenesulfonyl chloride; trifluoroacetic acid; N,N,N',N'-tetramethylguanidine;
In
methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene;
7.1: |Michael Addition;
DOI:10.1016/j.tet.2013.07.093