Multi-step reaction with 12 steps
1.1: methanol; lithium borohydride / diethyl ether / 6 h / 20 °C
2.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane / 20 h / 20 °C
3.1: (+)-Ipc2BOMe / diethyl ether / 3 h / -78 - 20 °C
4.1: 1H-imidazole; dmap / dichloromethane / 12 h / 20 °C
5.1: ozone / dichloromethane / 1 h / -78 °C
5.2: 6 h / 20 °C
6.1: diethyl ether / 4 h / -78 °C
7.1: pyridine; Dess-Martin periodane / dichloromethane / 15 h / 20 °C
8.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 24 h / 40 °C
9.1: (triphenylphosphine)copper(I) hydride hexamer; phenylsilane / toluene / 24 h / 20 °C
10.1: methanol; pyridinium p-toluenesulfonate / dichloromethane / 0.5 h / 20 °C
11.1: acetic acid; tetramethylammonium triacetoxyborohydride / acetonitrile / 48 h / -20 °C
12.1: CSA / dichloromethane / 5 h / 20 °C
With
pyridine; 1H-imidazole; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; methanol; dmap; lithium borohydride; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; (triphenylphosphine)copper(I) hydride hexamer; [bis(acetoxy)iodo]benzene; phenylsilane; pyridinium p-toluenesulfonate; Dess-Martin periodane; ozone; acetic acid; tetramethylammonium triacetoxyborohydride;
In
diethyl ether; dichloromethane; toluene; acetonitrile;
DOI:10.1016/j.tetlet.2011.07.105