Multi-step reaction with 9 steps
1.1: n-butyllithium / tetrahydrofuran / 0.25 h / -78 °C / Inert atmosphere
1.2: 0.5 h / -78 °C / Inert atmosphere
2.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -78 °C
2.2: 2 h
3.1: sodium hydride / N,N-dimethyl-formamide / 0.33 h / 0 °C / Inert atmosphere
3.2: 80 °C / Inert atmosphere
4.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C
5.1: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / Inert atmosphere; Reflux
6.1: dichloromethane / 2 h / 20 °C / Inert atmosphere
7.1: tetra-(n-butyl)ammonium iodide; sodium hydride / tetrahydrofuran / 20 h / Inert atmosphere; Reflux
8.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C / Inert atmosphere
9.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1 h / 20 °C
With
lithium aluminium tetrahydride; n-butyllithium; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; sodium hydrogencarbonate; Dess-Martin periodane; trifluoroacetic acid; lithium hexamethyldisilazane;
In
tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ol301672y