Multi-step reaction with 21 steps
1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 20 °C
2.1: 1,1,3,3-Tetramethyldisiloxane / (Ph3P)2IrCl(CO) / toluene / 2 h / 20 °C
3.1: hydroquinone / acetonitrile / 95 °C
4.1: methyl p-toluene sulfonate / water / 2 h / 110 °C
4.2: 4 h / 95 °C
5.1: hydrogen / rhodium contaminated with carbon / tetrahydrofuran / 7 h / 20 °C / 760.05 Torr
6.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 20 °C
7.1: diisobutylaluminium hydride / dichloromethane / 2 h / -78 °C
7.2: Cooling with ice
8.1: triphenylphosphine / dichloromethane / 0.33 h / Cooling with ice
8.2: 0.33 h / Cooling with ice
9.1: n-butyllithium / hexane; tetrahydrofuran / -78 °C
9.2: 1 h / Cooling with ice
10.1: pyridine / methanol / 20 °C
11.1: iodine / acetonitrile / 3 h
12.1: potassium phosphate / bis-triphenylphosphine-palladium(II) chloride / N,N-dimethyl-formamide; water / 80 °C / Inert atmosphere
13.1: trifluoroacetic acid / chloroform
14.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / chloroform
15.1: lithium hexamethyldisilazane / N,N,N,N,N,N-hexamethylphosphoric triamide; tetrahydrofuran
16.1: dihydrogen peroxide; lithium hydroxide monohydrate / water; tetrahydrofuran
17.1: potassium carbonate / N,N-dimethyl-formamide
18.1: hydrogen / palladium on activated charcoal / tetrahydrofuran; methanol / 760.05 Torr
19.1: sodium hydrogencarbonate; Dess-Martin periodane / chloroform
20.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide
21.1: hydrogen bromide; acetic acid / water
With
pyridine; dmap; potassium phosphate; n-butyllithium; lithium hydroxide monohydrate; 1,1,3,3-Tetramethyldisiloxane; hydrogen bromide; hydrogen; dihydrogen peroxide; iodine; diisobutylaluminium hydride; sodium hydrogencarbonate; potassium carbonate; benzotriazol-1-ol; Dess-Martin periodane; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; hydroquinone; methyl p-toluene sulfonate; triphenylphosphine; trifluoroacetic acid; lithium hexamethyldisilazane;
bis-triphenylphosphine-palladium(II) chloride; palladium on activated charcoal; rhodium contaminated with carbon; (Ph3P)2IrCl(CO);
In
tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; dichloromethane; chloroform; water; N,N-dimethyl-formamide; toluene; acetonitrile;