Multi-step reaction with 10 steps
1.1: toluene / Reflux; Inert atmosphere
2.1: titanium(IV) isopropylate; titanium tetrachloride / dichloromethane / 0.17 h / Inert atmosphere
2.2: 0.33 h / -30 °C / Inert atmosphere
3.1: N,O-bis-(trimethylsilyl)-acetamide / toluene / 1 h / 90 °C / Inert atmosphere
3.2: 21 h / 45 °C / Inert atmosphere
4.1: formic acid / dichloromethane / 16 h / 20 °C / Inert atmosphere
5.1: triethylamine; lithium chloride / water; acetonitrile / 18 h / 20 °C / Inert atmosphere
6.1: 4-methyl-morpholine; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate / dichloromethane / 1 h / 20 °C / Inert atmosphere
7.1: formic acid / 6 h / 35 °C / Inert atmosphere
8.1: sodium tetrahydroborate / methanol / Inert atmosphere
9.1: 4-methyl-morpholine; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate / N,N-dimethyl-formamide / 1 h / 20 °C / Inert atmosphere
9.2: 1 h / 20 °C / Inert atmosphere
10.1: tert-butylamine / acetone / 70 h / 35 °C / Inert atmosphere
With
4-methyl-morpholine; titanium(IV) isopropylate; sodium tetrahydroborate; formic acid; N,O-bis-(trimethylsilyl)-acetamide; titanium tetrachloride; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; tert-butylamine; triethylamine; lithium chloride;
In
methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; acetonitrile;
DOI:10.1021/op200314z