Multi-step reaction with 15 steps
1.1: camphor-10-sulfonic acid / dichloromethane / 16 h / 20 °C
2.1: diisobutylaluminium hydride / tetrahydrofuran; hexane / 3 h / -78 - -20 °C
2.2: 0.5 h / 20 °C
3.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 0.5 h / 20 °C
4.1: titanium tetrachloride / dichloromethane / 0.33 h / -50 °C
4.2: 2 h / -40 °C
4.3: 2 h / -78 °C
5.1: 2,6-dimethylpyridine / dichloromethane / 3 h / -78 - 20 °C
6.1: dihydrogen peroxide; lithium hydroxide / tetrahydrofuran; water / 3 h / 0 - 20 °C
7.1: N-ethyl-N,N-diisopropylamine; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; benzotriazol-1-ol / dichloromethane / 2 h / 20 °C
7.2: 72 h / 20 °C
8.1: diethylamino-sulfur trifluoride / dichloromethane / 2 h / -78 °C
9.1: copper(ll) bromide; hexamethylenetetramine; 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 2 h / 20 °C
10.1: diisobutylaluminium hydride / dichloromethane; toluene / 0.75 h / -78 °C
11.1: potassium carbonate / methanol / 0 - 20 °C
12.1: Schwartz's reagent / tetrahydrofuran / 1 h / 0 °C
12.2: 0.67 h / -78 °C / Darkness
13.1: tert.-butyl lithium / pentane; diethyl ether / 1 h / -78 °C / Inert atmosphere
13.2: 0.25 h / -78 °C
13.3: 3 h / -78 °C
14.1: dmap; pyridine / dichloromethane / 16 h / 20 °C
15.1: pyridine; hydrogenchloride; hydrogen fluoride / tetrahydrofuran; water / 14 h / 20 °C
With
pyridine; 2,6-dimethylpyridine; hydrogenchloride; dmap; Schwartz's reagent; diethylamino-sulfur trifluoride; hexamethylenetetramine; camphor-10-sulfonic acid; hydrogen fluoride; dihydrogen peroxide; tert.-butyl lithium; titanium tetrachloride; diisobutylaluminium hydride; sodium hydrogencarbonate; potassium carbonate; benzotriazol-1-ol; Dess-Martin periodane; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; copper(ll) bromide; lithium hydroxide;
In
tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; toluene; pentane;
DOI:10.1039/c2ob26256h