Multi-step reaction with 13 steps
1.1: trichlorophosphate / mineral oil / 2 h / 0 - 23 °C / Inert atmosphere
1.2: 1 h / 23 °C / Cooling with ice
2.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -78 °C
2.2: 2 h / -78 °C
3.1: Dess-Martin periodane / dichloromethane; water / 2 h / 23 °C
4.1: manganese(III) triacetate dihydrate; acetic acid / 0 - 60 °C / Inert atmosphere
5.1: lithium hydroxide / tetrahydrofuran; water / 0.5 h / 23 °C
5.2: 0 - 23 °C / Inert atmosphere
6.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -78 - 0 °C
7.1: calcium borohydride bis(tetrahydrofuran) / tetrahydrofuran / 0.5 h / 0 - 23 °C
7.2: 0.5 h / 0 - 50 °C
8.1: trifluoroacetic acid / dichloromethane / 0.5 h / 0 °C / Inert atmosphere
9.1: water; Dess-Martin periodane / dichloromethane / 0.25 h / 40 °C
10.1: hydrogenchloride / methanol; water / 2 h / 0 - 40 °C
11.1: potassium hydrogen phthalate / methanol; water / 10 - 15 °C / pH 3.7
11.2: 110 °C
12.1: triphenylphosphine / tetrahydrofuran; water / 1 h / 80 °C
12.2: 23 °C
13.1: triethylamine / N,N-dimethyl-formamide / 5 h / 70 °C
With
hydrogenchloride; calcium borohydride bis(tetrahydrofuran); water; potassium hydrogen phthalate; manganese(III) triacetate dihydrate; Dess-Martin periodane; acetic acid; triethylamine; triphenylphosphine; trifluoroacetic acid; lithium hydroxide; lithium hexamethyldisilazane; trichlorophosphate;
In
tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; mineral oil;
5.2: Mitsunobu reaction / 12.1: Staudinger reaction;
DOI:10.1039/c0cc02214d