Multi-step reaction with 10 steps
1.1: water; sodium hydroxide / methanol / 16 h / 20 °C / Inert atmosphere
2.1: pyridine; trifluoro-[1,3,5]triazine / dichloromethane / -10 - 20 °C / Inert atmosphere
3.1: sodium tetrahydroborate / methanol; dichloromethane / 2 h / 20 °C / Inert atmosphere
4.1: sodium hydride / tetrahydrofuran / 0.5 h / Inert atmosphere
4.2: 4 h / 20 °C / Inert atmosphere
5.1: TurboGrignard / tetrahydrofuran / 0.5 h / Inert atmosphere
5.2: 16 h / 20 °C / Inert atmosphere
6.1: Dess-Martin periodane / dichloromethane / 16 h / 20 °C / Inert atmosphere
7.1: hydrazine hydrate / ethanol / 2 h / 80 °C / Inert atmosphere
8.1: pyridine; trichlorophosphate / 2 h / 50 °C / Inert atmosphere
9.1: ammonium cerium (IV) nitrate; water / acetonitrile / 2 h / 20 °C / Inert atmosphere
10.1: ammonia; iodine / water / 3 h / 60 °C / Inert atmosphere
With
pyridine; sodium tetrahydroborate; TurboGrignard; trifluoro-[1,3,5]triazine; ammonium cerium (IV) nitrate; ammonia; water; iodine; sodium hydride; Dess-Martin periodane; hydrazine hydrate; sodium hydroxide; trichlorophosphate;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; water; acetonitrile;
6.1: Dess-Martin oxidation;
DOI:10.1021/ml2000438