Multi-step reaction with 11 steps
1.1: diisobutylaluminium hydride / dichloromethane; toluene / 120.25 h / -78 - -13 °C / Inert atmosphere
2.1: pyridine / dichloromethane / -78 °C / Inert atmosphere
3.1: 2,6-dimethylpyridine / dichloromethane / 1 h / 20 °C / Inert atmosphere
4.1: diisobutylaluminium hydride / dichloromethane; toluene / 1 h / -78 - 0 °C / Inert atmosphere
4.2: 2 h / 0 - 20 °C / Inert atmosphere
5.1: Dess-Martin periodane / dichloromethane; water / 1 h / 0 - 20 °C
6.1: barium hydroxide octahydrate / tetrahydrofuran; water / 20 °C / Inert atmosphere
7.1: sodium tetrahydroborate / methanol / 20 °C / Inert atmosphere
8.1: 2,6-dimethylpyridine / dichloromethane / 0.5 h / 20 °C / Inert atmosphere
9.1: potassium hydroxide / tetrahydrofuran; water / 12 h / 100 °C / Inert atmosphere
10.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / toluene / 1 h / 20 °C / Inert atmosphere
10.2: 1 h / Inert atmosphere
11.1: triethylamine; caesium carbonate; palladium diacetate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere
With
pyridine; 2,6-dimethylpyridine; sodium tetrahydroborate; barium hydroxide octahydrate; 2,4,6-trichlorobenzoyl chloride; palladium diacetate; diisobutylaluminium hydride; caesium carbonate; Dess-Martin periodane; triethylamine; potassium hydroxide;
In
tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene;
5.1: |Dess-Martin Oxidation / 6.1: |Horner-Wadsworth-Emmons Olefination / 11.1: |Heck Reaction;
DOI:10.1021/ol400014e