Multi-step reaction with 12 steps
1.1: toluene / 20 h / 100 °C
2.1: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / toluene / 2.25 h / 95 °C
3.1: lithium aluminium tetrahydride / diethyl ether / 0.5 h / 0 °C
4.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.75 h / -78 °C
4.2: 0.17 h
5.1: tert.-butyl lithium / diethyl ether; pentane / 0.58 h / -78 - 20 °C
5.2: 0.5 h / -78 °C
6.1: pyridinium p-toluenesulfonate / dichloromethane / 14 h
7.1: palladium 10% on activated carbon; hydrogen / isopropyl alcohol / 18 h
8.1: tributylphosphine / tetrahydrofuran / 15 h / 0 - 20 °C
9.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / acetonitrile / 12 h / 20 °C
10.1: pyridine hydrogenfluoride / tetrahydrofuran / 24 h / 0 °C
11.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.75 h / -78 °C
11.2: 0.17 h
12.1: n-butyllithium / tetrahydrofuran; hexane / 2.75 h / -45 - 20 °C
12.2: 2.5 h / -78 - 20 °C
With
lithium aluminium tetrahydride; n-butyllithium; tetrapropylammonium perruthennate; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); tributylphosphine; palladium 10% on activated carbon; hydrogen; tert.-butyl lithium; tri-n-butyl-tin hydride; pyridinium p-toluenesulfonate; pyridine hydrogenfluoride; dimethyl sulfoxide; 4-methylmorpholine N-oxide;
In
tetrahydrofuran; diethyl ether; hexane; dichloromethane; isopropyl alcohol; toluene; acetonitrile; pentane;
DOI:10.1002/anie.201203935