Multi-step reaction with 13 steps
1.1: 1H-imidazole / tetrahydrofuran / 24 h / 0 - 20 °C
2.1: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / 0 - 20 °C
3.1: potassium iodide; sodium hydride / tetrahydrofuran / 6 h / 60 °C
4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 20 °C
5.1: Dess-Martin periodane / dichloromethane / 1 h / 0 °C / Inert atmosphere
6.1: dichloromethane / 2 h / 20 °C / Inert atmosphere
7.1: diisobutylaluminium hydride / dichloromethane; toluene / 1 h / 78 °C / Inert atmosphere
8.1: titanium(IV) isopropylate; L-(+)-diisopropyl tartrate / dichloromethane / 0.5 h / -30 °C / Inert atmosphere
8.2: 15 h / -30 °C / Inert atmosphere
9.1: Dess-Martin periodane / dichloromethane / 1 h / 0 °C / Inert atmosphere
10.1: dichloromethane / 2 h / 20 °C / Inert atmosphere
11.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 7 h / -30 - 20 °C / Inert atmosphere
12.1: diisobutylaluminium hydride / dichloromethane; toluene / 0.67 h / -78 °C / Inert atmosphere
13.1: triethylamine; dmap / dichloromethane / 1 h / 20 °C
With
1H-imidazole; titanium(IV) isopropylate; dmap; lithium aluminium tetrahydride; L-(+)-diisopropyl tartrate; trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; sodium hydride; diisobutylaluminium hydride; Dess-Martin periodane; triethylamine; potassium iodide;
In
tetrahydrofuran; dichloromethane; toluene;
5.1: |Dess-Martin Oxidation / 6.1: |Wittig Olefination / 9.1: |Dess-Martin Oxidation / 10.1: |Wittig Olefination;
DOI:10.1016/j.tet.2013.03.012