Multi-step reaction with 9 steps
1.1: camphor-10-sulfonic acid / dichloromethane / 16 h / Inert atmosphere; Schlenk technique
2.1: diisobutylaluminium hydride / dichloromethane / 4.42 h / -78 °C / Inert atmosphere; Schlenk technique
3.1: Dess-Martin periodane / dichloromethane / 3 h / 0 - 23 °C / Inert atmosphere; Schlenk technique
4.1: diethylzinc / toluene / 1 h / Inert atmosphere; Schlenk technique; Reflux
4.2: 1 h / 23 °C / Inert atmosphere; Schlenk technique
4.3: Inert atmosphere; Schlenk technique
5.1: 2,6-dimethylpyridine / dichloromethane / 1 h / -78 °C / Inert atmosphere; Schlenk technique
6.1: potassium carbonate / methanol / 1 h / 23 °C / Inert atmosphere; Schlenk technique
7.1: diisobutylaluminium hydride; zirconocene dichloride; iodine / tetrahydrofuran / 1 h / -78 - 23 °C / Inert atmosphere; Schlenk technique
8.1: diethylzinc / toluene / 1 h / Inert atmosphere; Schlenk technique; Reflux
8.2: 1 h / 23 °C / Inert atmosphere; Schlenk technique
8.3: Inert atmosphere; Schlenk technique
9.1: triethylamine; 2,4,6-trichlorobenzoyl chloride; dmap / toluene / 3 h / 0 - 23 °C / Inert atmosphere; Schlenk technique
With
2,6-dimethylpyridine; dmap; zirconocene dichloride; 2,4,6-trichlorobenzoyl chloride; camphor-10-sulfonic acid; iodine; diethylzinc; diisobutylaluminium hydride; potassium carbonate; Dess-Martin periodane; triethylamine;
In
tetrahydrofuran; methanol; dichloromethane; toluene;
DOI:10.1039/c2ob26906f