Multi-step reaction with 11 steps
1.1: silver nitrate; calcium carbonate / water; acetone / 4 h / Inert atmosphere; Darkness
2.1: N-Bromosuccinimide; water / 48 h / 10 °C / Inert atmosphere; Darkness
3.1: water; sodium hydrogencarbonate / methanol / Inert atmosphere
4.1: 2,6-dimethylpyridine / dichloromethane / 0 - 20 °C / Inert atmosphere
5.1: trichloroacetic acid / tetrahydrofuran; water / Inert atmosphere
6.1: pyridine; Dess-Martin periodane / dichloromethane / 4 h / 0 °C / Inert atmosphere
7.1: tert.-butyl lithium / diethyl ether; pentane / 0.08 h / -78 °C / Inert atmosphere
7.2: 0.42 h / -78 °C / Inert atmosphere
8.1: pyridine; Dess-Martin periodane / dichloromethane / 0 - 20 °C / Inert atmosphere
9.1: sodium tetrahydroborate; cerium(III) chloride heptahydrate / methanol / -70 °C / Inert atmosphere
10.1: lithium hexamethyldisilazane / tetrahydrofuran / -78 °C / Inert atmosphere
10.2: -78 - 20 °C / Inert atmosphere
11.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 0 - 20 °C / Inert atmosphere
11.2: Inert atmosphere
With
pyridine; 2,6-dimethylpyridine; sodium tetrahydroborate; N-Bromosuccinimide; cerium(III) chloride heptahydrate; water; tert.-butyl lithium; sodium hydrogencarbonate; Dess-Martin periodane; silver nitrate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; calcium carbonate; lithium hexamethyldisilazane; trichloroacetic acid;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; acetone; pentane;
6.1: Dess-Martin oxidation / 8.1: Dess-Martin oxidation / 9.1: Luche reduction;
DOI:10.1002/anie.201005850