Multi-step reaction with 13 steps
1.1: diethylamino-sulfur trifluoride / tetrahydrofuran / 1.5 h / -78 °C
1.2: -78 - 20 °C
2.1: hexamethylenetetramine; 1,8-diazabicyclo[5.4.0]undec-7-ene; copper(ll) bromide / dichloromethane / 0 - 20 °C
3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 0 - 20 °C
4.1: Dess-Martin periodane / dichloromethane / 0 - 20 °C
5.1: sodium hydride / tetrahydrofuran
6.1: dimethylsulfide borane complex; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole / tetrahydrofuran / 0 °C
7.1: dichloromethane / 0 - 20 °C
8.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride
8.2: 0 - 20 °C
9.1: lithium hydroxide monohydrate; water / tetrahydrofuran / 0 - 20 °C
10.1: 1-hydroxy-7-aza-benzotriazole; O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate
10.2: 0 - 20 °C
11.1: tetrahydrofuran; dichloromethane / 0 - 20 °C
12.1: 1-hydroxy-7-aza-benzotriazole; O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate
12.2: 0 - 20 °C
13.1: water; lithium hydroxide / tetrahydrofuran / 0 - 20 °C
With
1-hydroxy-7-aza-benzotriazole; lithium hydroxide monohydrate; O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; diethylamino-sulfur trifluoride; dimethylsulfide borane complex; hexamethylenetetramine; tetrabutyl ammonium fluoride; water; sodium hydride; benzotriazol-1-ol; Dess-Martin periodane; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; copper(ll) bromide; lithium hydroxide; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole;
In
tetrahydrofuran; dichloromethane;
4.1: Dess-Martin oxidation;
DOI:10.1055/s-0030-1260806