Multi-step reaction with 13 steps
1.1: 1H-imidazole; dmap / dichloromethane / 2 h / 20 °C
2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1.25 h / -70 °C
2.2: 2 h / -70 - 20 °C
3.1: dimethyl zinc(II); tert.-butyl lithium / tetrahydrofuran; n-heptane; pentane / 1.75 h / -70 °C / Inert atmosphere
3.2: 3 h / -70 °C / Inert atmosphere
4.1: pyridinium p-toluenesulfonate / tetrahydrofuran; methanol
5.1: pyridinium p-toluenesulfonate
6.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 4 h / Reflux; Inert atmosphere
7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 0 °C
8.1: quinoline; hydrogen / hexane; ethyl acetate / 1.5 h
9.1: diisobutylaluminium hydride / hexane; dichloromethane / 0.25 h / 0 °C
10.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / 0 °C
10.2: 2 h / 0 °C
11.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 11 h
12.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 20 °C
13.1: Hoveyda-Grubbs catalyst second generation / dichloromethane / 14 h / 20 °C / Inert atmosphere
With
1H-imidazole; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; quinoline; dmap; Hoveyda-Grubbs catalyst second generation; oxalyl dichloride; tetrabutyl ammonium fluoride; hydrogen; dimethyl zinc(II); tert.-butyl lithium; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine;
In
tetrahydrofuran; methanol; hexane; n-heptane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; mineral oil; pentane;
2.1: Swern oxidation / 2.2: Swern oxidation / 3.2: Felkin-Anh addition;
DOI:10.1021/ol201920j