Multi-step reaction with 10 steps
1.1: 2,6-dimethylpyridine / dichloromethane / 14 h / 0 °C / Inert atmosphere
2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 1 h / Inert atmosphere; Reflux
3.1: lithium aluminium tetrahydride / tetrahydrofuran / 3.5 h / 0 °C / Inert atmosphere
4.1: manganese(IV) oxide / dichloromethane / 16 h / 20 °C / Inert atmosphere
5.1: 2,6-dimethylpyridine / dichloromethane / 0.5 h / 0 - 20 °C / Inert atmosphere
6.1: copper(l) iodide / diethyl ether / 1 h / -78 - 0 °C / Inert atmosphere
6.2: 1 h / -78 °C / Inert atmosphere
7.1: tert.-butyl lithium / pentane; diethyl ether / 0.58 h / -78 - 20 °C / Inert atmosphere
7.2: 5 h / -78 °C / Inert atmosphere
8.1: pyridine; ozone; Sudan III / methanol; dichloromethane / -78 °C / Inert atmosphere
8.2: 12 h / 20 °C / Inert atmosphere
9.1: sodium tetrahydroborate / dichloromethane; ethanol / 24 h / 20 °C / Inert atmosphere
10.1: pyridinium p-toluenesulfonate / 24 h / 20 °C / Inert atmosphere
With
pyridine; 2,6-dimethylpyridine; manganese(IV) oxide; sodium tetrahydroborate; copper(l) iodide; lithium aluminium tetrahydride; tert.-butyl lithium; pyridinium p-toluenesulfonate; ozone; 1,8-diazabicyclo[5.4.0]undec-7-ene; Sudan III;
In
tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; pentane;
DOI:10.1002/ejoc.201301616