Multi-step reaction with 14 steps
1.1: N-Bromosuccinimide; water / 48 h / 10 °C / Inert atmosphere; Darkness
2.1: water; sodium hydrogencarbonate / methanol / Inert atmosphere
3.1: 2,6-dimethylpyridine / dichloromethane / 0 - 20 °C / Inert atmosphere
4.1: trichloroacetic acid / tetrahydrofuran; water / Inert atmosphere
5.1: pyridine; Dess-Martin periodane / dichloromethane / 4 h / 0 °C / Inert atmosphere
6.1: tert.-butyl lithium / diethyl ether; pentane / 0.08 h / -78 °C / Inert atmosphere
6.2: 0.42 h / -78 °C / Inert atmosphere
7.1: pyridine; Dess-Martin periodane / dichloromethane / 0 - 20 °C / Inert atmosphere
8.1: sodium tetrahydroborate; cerium(III) chloride heptahydrate / methanol / -70 °C / Inert atmosphere
9.1: lithium hexamethyldisilazane / tetrahydrofuran / -78 °C / Inert atmosphere
9.2: -78 - 20 °C / Inert atmosphere
10.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 0 - 20 °C / Inert atmosphere
10.2: Inert atmosphere
11.1: 1H-imidazole; iodine; triphenylphosphine / dichloromethane / 2 h / Inert atmosphere
12.1: lithium diethylamide / tetrahydrofuran / 0.58 h / -78 °C / Inert atmosphere
12.2: 2.5 h / -78 °C / Inert atmosphere
13.1: diisobutylaluminium hydride / toluene / 2.5 h / -40 °C / Inert atmosphere
13.2: -40 °C / Inert atmosphere
14.1: dmap; N-ethyl-N,N-diisopropylamine / dichloromethane / 16 h / 0 - 20 °C / Inert atmosphere
With
pyridine; 1H-imidazole; 2,6-dimethylpyridine; dmap; sodium tetrahydroborate; N-Bromosuccinimide; cerium(III) chloride heptahydrate; lithium diethylamide; water; iodine; tert.-butyl lithium; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium hexamethyldisilazane; trichloroacetic acid;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; toluene; pentane;
5.1: Dess-Martin oxidation / 7.1: Dess-Martin oxidation / 8.1: Luche reduction;
DOI:10.1002/anie.201005850