Multi-step reaction with 11 steps
1.1: toluene / 4 h / 180 °C / Inert atmosphere
2.1: C32H12BF24(1-)*C39H50IrNOP(1+); hydrogen / dichloromethane / 18 h / 20 °C / 60006 - 67506.8 Torr / Inert atmosphere; Autoclave
3.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.75 h / -78 °C / Inert atmosphere
3.2: -78 °C / Inert atmosphere
4.1: sodium tetrahydroborate / tetrahydrofuran; water / 18 h / 0 °C / Inert atmosphere
5.1: 1H-imidazole; dmap / dichloromethane / 1 h / 0 °C / Inert atmosphere
6.1: methanol; potassium carbonate / 18 h / 20 °C / Inert atmosphere
7.1: pyridine; dmap / dichloromethane / 18 h / 40 °C / Inert atmosphere
8.1: magnesium / diethyl ether / 2 h / Inert atmosphere; Reflux
8.2: -20 - 20 °C / Inert atmosphere
9.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 4 h / Inert atmosphere
10.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / tetrahydrofuran; dimethyl sulfoxide / 5 h / 20 °C / Inert atmosphere
11.1: triethylamine; dicyclohexyl(((trifluoromethyl)sulfonyl)oxy)borane / dichloromethane / 5 h / -78 °C / Inert atmosphere
11.2: 3 h / -78 °C / Inert atmosphere
With
pyridine; 1H-imidazole; methanol; dmap; sodium tetrahydroborate; C32H12BF24(1-)*C39H50IrNOP(1+); tetrabutyl ammonium fluoride; hydrogen; sodium hexamethyldisilazane; potassium carbonate; magnesium; triethylamine; dicyclohexyl(((trifluoromethyl)sulfonyl)oxy)borane; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione;
In
tetrahydrofuran; diethyl ether; dichloromethane; water; dimethyl sulfoxide; toluene;
1.1: Cope rearrangement;
DOI:10.1021/jo202330b