CHELIDONINE synthesis

Yield:-

Steps:

Multi-step reaction with 10 steps
1.1: silver carbonate; palladium diacetate / benzene / 16 h / Reflux
2.1: (S)-(-)-2-phenyl-2,3-dihydrobenzo[d]imidazo[2,1-b]thiazole; C₅₃H₅₀IrNO₂P⁽¹⁺⁾*BF₄^(1-); N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 24 h / 20 °C / Inert atmosphere
2.2: 0.5 h / 20 °C
3.1: sodium tetrahydroborate; methanol / 0.5 h / 0 °C
4.1: potassium hydroxide / 2 h / 0 - 20 °C
5.1: triphenylphosphine; carbon tetrabromide / dichloromethane / 0.5 h / 0 - 20 °C
6.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 3 h / 0 - 20 °C
7.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / toluene / 1 h / 70 °C / Inert atmosphere
8.1: N-Bromosuccinimide; water / tetrahydrofuran / 1.5 h / 20 °C
9.1: potassium tert-butylate / tetrahydrofuran / 0.75 h / -78 °C
10.1: lithium aluminium tetrahydride / tetrahydrofuran; 1,4-dioxane / 17 h / Reflux

References:

Fyfe, James W. B.;Hutchings-Goetz, Luke S.;Snaddon, Thomas N.;Yang, Chao [Angewandte Chemie - International Edition,2020,vol. 59,# 40,p. 17556 - 17564][Angew. Chem.,2020,vol. 132,# 40,p. 17709 - 17717,9]