Multi-step reaction with 23 steps
1.1: N,N,N',N'-tetramethylguanidine / dichloromethane / 48 h / 20 °C
2.1: (+)-1,2-bis-[(2S,5S)-2,5-diethylphospholano]benzene (1,5-cycloctadiene)rhodium(I) trifluoromethanesulfonate; hydrogen / ethyl acetate / 72 h / 50 °C / 25858.1 Torr
3.1: methanol; acetyl chloride / 0 - 20 °C
4.1: triethylamine / dichloromethane / 0 - 20 °C
5.1: water; lithium hydroxide / tetrahydrofuran; methanol / 0 - 20 °C
6.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine / dichloromethane / 24 h / 0 - 20 °C
7.1: diisobutylaluminium hydride / toluene / 1.5 h / -78 °C / Inert atmosphere
7.2: 1 h / 20 °C
8.1: water; toluene-4-sulfonic acid / methanol / 1.5 h / 20 °C / Reflux
9.1: 10% Pd/C; hydrogen / methanol / 48 h / 20 °C / 760.05 Torr
10.1: formic acid; sodium sulfate / dichloromethane / 24 h / 0 - 20 °C
11.1: potassium carbonate / acetone / 41.5 h / 0 - 20 °C
12.1: pyridine / dichloromethane / 1 h / 0 - 20 °C
13.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; 2-hydroxyethanethiol / acetonitrile / 2 h / 0 - 20 °C
14.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 23.5 h / 0 - 20 °C
15.1: N-Bromosuccinimide / dichloromethane / 0.5 h / 0 °C
16.1: trifluoroacetic acid / dichloromethane / 0.42 h / 0 °C
17.1: pyridine / dichloromethane / 0.5 h / 0 °C
18.1: triethylamine / 1 h / 20 °C
19.1: 1H-imidazole / N,N-dimethyl-formamide / 1 h / 0 - 20 °C
20.1: sodium tetrahydroborate; lithium chloride / tetrahydrofuran; ethanol / 48 h / 0 - 20 °C
21.1: boron trifluoride diethyl etherate / dichloromethane / 1.92 h / 0 °C
22.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / tetrahydrofuran / 0 °C / Reflux
23.1: sodium iodide / N,N-dimethyl-formamide / 18 h / 110 °C
With
pyridine; 1H-imidazole; methanol; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium tetrahydroborate; N-Bromosuccinimide; formic acid; (+)-1,2-bis-[(2S,5S)-2,5-diethylphospholano]benzene (1,5-cycloctadiene)rhodium(I) trifluoromethanesulfonate; 10% Pd/C; boron trifluoride diethyl etherate; water; hydrogen; diisobutylaluminium hydride; potassium carbonate; benzotriazol-1-ol; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; sodium sulfate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; acetyl chloride; trifluoroacetic acid; 2-hydroxyethanethiol; sodium iodide; lithium chloride; lithium hydroxide; N,N,N',N'-tetramethylguanidine;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetone; toluene; acetonitrile;
1.1: |Horner-Wadsworth-Emmons Olefination / 10.1: |Pictet-Spengler Synthesis;
DOI:10.1055/s-0032-1316579