Multi-step reaction with 9 steps
1: 100 percent / Na2CO3 / acetone; H2O / 2 h / 20 °C
2: 86 percent / LiOH
3: 93 percent / I2; Ag2SO4 / methanol / 1.5 h / 20 °C
4: 95 percent / [PdCl2(dppf)]*CH2Cl2; KOAc / dimethylsulfoxide / 13 h / 80 °C
5: [PdCl2(dppf)]*CH2Cl2; KOAc / 1,2-dimethoxy-ethane / 2 h / 80 °C
6: LiOH / tetrahydrofuran; H2O / 1.5 h / 0 °C
7: 1-[3-dimethylaminopropyl]-3-ethylcarbodiimide hydrochloride; 1-hydroxy-7-azabenzotriazole / tetrahydrofuran / 2 h / 20 °C
8: OsO4; 4-methylmorpholine N-oxide; 1,4-bis(9-O-dihydroquinidine)phthalazine / 2-methyl-propan-2-ol; H2O / 1 h / 20 °C
9: TFA / CH2Cl2 / 2 h / 20 °C
With
(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; (3a,9R,3'''a,4'"b,9'"R)-9,9'-[1,4-phthalazinediylbis(oxy)]bis[6'-(methyloxy)-10,11-dihydrocinchonan]; lithium hydroxide; osmium(VIII) oxide; 1-hydroxy-7-aza-benzotriazole; iodine; potassium acetate; sodium carbonate; silver sulfate; 4-methylmorpholine N-oxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid;
In
tetrahydrofuran; methanol; 1,2-dimethoxyethane; dichloromethane; water; dimethyl sulfoxide; acetone; tert-butyl alcohol;
4: Miyaura reaction / 5: Suzuki-Miyaura reaction;
DOI:10.1021/ja049821k