Multi-step reaction with 13 steps
1.1: N-iodo-succinimide; methanesulfonic acid / acetic acid / 6 h / 20 °C / Inert atmosphere
2.1: bis-triphenylphosphine-palladium(II) chloride; 1,2,2,6,6-pentamethylpiperidine / N,N-dimethyl-formamide / 12 h / 130 °C / Inert atmosphere
3.1: sodium hydride / dimethyl sulfoxide; mineral oil / 4 h / 20 °C / Inert atmosphere
4.1: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / benzene / 5 h / 80 °C / Inert atmosphere
5.1: sodium tetrahydroborate / ethanol / 1 h / 20 °C / Inert atmosphere
6.1: toluene-4-sulfonic acid / toluene / 1 h / 80 °C / Inert atmosphere
7.1: diethylzinc; trifluoroacetic acid / dichloromethane; hexane / 0.33 h / 0 °C / Inert atmosphere
7.2: 12 h / 20 °C / Inert atmosphere
8.1: boron trichloride / dichloromethane / 0.5 h / 20 °C / Inert atmosphere
9.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 20 °C / Inert atmosphere
10.1: bis-triphenylphosphine-palladium(II) chloride; lithium chloride / N,N-dimethyl-formamide / 12 h / 100 °C / Inert atmosphere
11.1: pyridine hydrogenfluoride / acetonitrile / 0.5 h / 20 °C / Inert atmosphere
12.1: triethylamine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere
13.1: dichloromethane / 1 h / 0 °C / Inert atmosphere
With
1,2,2,6,6-pentamethylpiperidine; bis-triphenylphosphine-palladium(II) chloride; sodium tetrahydroborate; N-iodo-succinimide; methanesulfonic acid; 2,2'-azobis(isobutyronitrile); diethylzinc; tri-n-butyl-tin hydride; boron trichloride; sodium hydride; toluene-4-sulfonic acid; pyridine hydrogenfluoride; triethylamine; trifluoroacetic acid; lithium chloride;
In
tetrahydrofuran; ethanol; hexane; dichloromethane; acetic acid; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; acetonitrile; mineral oil; benzene;
2.1: |Heck Reaction / 4.1: |Dowd Ring Expansion / 10.1: |Stille Cross Coupling;
DOI:10.1021/ol501423t