Multi-step reaction with 20 steps
1.1: silver trifluoromethanesulfonate; (trimethylphosphine)gold(I) chloride / toluene / 40 °C / Inert atmosphere
2.1: toluene-4-sulfonic acid / water / Inert atmosphere
2.2: 65 °C / Inert atmosphere
2.3: -78 - 23 °C / Inert atmosphere
3.1: potassium carbonate; N-iodo-succinimide / 23 °C / Inert atmosphere
4.1: acetic acid / water; tetrahydrofuran / 75 °C / Inert atmosphere
5.1: sodium tetrahydroborate / methanol / 0 °C / Inert atmosphere
6.1: toluene-4-sulfonic acid / benzene / 80 °C / Inert atmosphere
7.1: Dess-Martin periodane / dichloromethane / 40 °C / Inert atmosphere
8.1: trifluoroacetic acid / 1,2-dichloro-ethane / 12 h / 40 °C / Inert atmosphere
9.1: trifluoroacetic acid; triethylsilane / 1,2-dichloro-ethane / 1 h / 23 °C / Inert atmosphere
10.1: sodium hydroxide / tetrahydrofuran; water / 14 h / 23 °C / Inert atmosphere
11.1: dichloromethane; hexane / 0.5 h / 23 °C / Inert atmosphere
12.1: dmap; triethylamine / dichloromethane / 2 h / 23 °C / Inert atmosphere
13.1: caesium carbonate / acetonitrile / 46 h / 40 °C / Inert atmosphere
14.1: tetrahydrofuran / 32 h / 60 °C / Inert atmosphere
15.1: pyridinium chlorochromate / dichloromethane / 2 h / 23 °C / Inert atmosphere
16.1: caesium carbonate / tetrahydrofuran / 12 h / 23 °C / Inert atmosphere
17.1: dmap; triethylamine / dichloromethane / 0.25 h / 23 °C / Inert atmosphere
18.1: 2-methyl-but-2-ene; sodium dihydrogenphosphate; sodium chlorite / tetrahydrofuran; water; tert-butyl alcohol / 18 h / 23 °C / Inert atmosphere
19.1: methanol; tetrahydrofuran / 0.25 h / 23 °C / Inert atmosphere
20.1: ethanol / 7 h / 55 °C / Inert atmosphere
With
triethylsilane; dmap; sodium chlorite; sodium tetrahydroborate; sodium dihydrogenphosphate; N-iodo-succinimide; 2-methyl-but-2-ene; (trimethylphosphine)gold(I) chloride; ethanol; silver trifluoromethanesulfonate; potassium carbonate; caesium carbonate; Dess-Martin periodane; toluene-4-sulfonic acid; acetic acid; triethylamine; pyridinium chlorochromate; trifluoroacetic acid; sodium hydroxide;
In
tetrahydrofuran; methanol; hexane; dichloromethane; water; 1,2-dichloro-ethane; toluene; acetonitrile; tert-butyl alcohol; benzene;
2.3: |Wittig Olefination / 8.1: |Fischer Indole Synthesis;
DOI:10.1021/jacs.8b03404