Multi-step reaction with 8 steps
1.1: 1H-imidazole / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere
2.1: diisobutylaluminium hydride / hexane; dichloromethane / 0.5 h / -78 °C / Inert atmosphere
3.1: potassium tert-butylate / tetrahydrofuran / 1 h / 0 - 20 °C / Inert atmosphere
3.2: 0 - 20 °C / Inert atmosphere
4.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C / Inert atmosphere
4.2: -78 - 20 °C / Inert atmosphere
5.1: tetrahydrofuran / 1 h / -78 °C / Inert atmosphere
5.2: Inert atmosphere
6.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 1.5 h / 0 - 20 °C / Inert atmosphere
7.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere
8.1: ammonia / methanol / 4 h / 80 °C / Inert atmosphere
With
1H-imidazole; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; oxalyl dichloride; potassium tert-butylate; ammonia; diisobutylaluminium hydride; dimethyl sulfoxide; triphenylphosphine; diethylazodicarboxylate;
In
tetrahydrofuran; methanol; hexane; dichloromethane;
3.2: Wittig reaction / 4.1: Swern oxidation / 4.2: Swern oxidation / 5.1: Grignard reaction / 5.2: Grignard reaction / 7.1: Mitsunobu reaction;
DOI:10.1016/j.bmc.2011.05.026