Multi-step reaction with 12 steps
1.1: triethylamine / dichloromethane / 2 h / 0 °C
2.1: caesium carbonate / N,N-dimethyl-formamide / 20 h / 100 °C
3.1: potassium hydroxide / water; ethanol / 2 h / 120 °C
3.2: 4 h / 20 °C
4.1: dimethylsulfide borane complex / tetrahydrofuran / 12 h / 0 °C
5.1: iodine; potassium carbonate / methanol; water / 24 h / 20 °C
6.1: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / benzene / 2 h / 90 °C
7.1: tri-n-butyl-tin hydride; Dess-Martin periodane / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere
8.1: potassium carbonate / methanol / 2 h / 0 - 20 °C / Inert atmosphere
9.1: triethylamine; tetrakis(triphenylphosphine) palladium(0); copper(II) sulfate; sodium L-ascorbate / N,N-dimethyl-formamide / 5 h / 80 °C / Inert atmosphere
10.1: sodium tetrachloroaurate(III) dihyrate / ethanol / 4 h / 20 °C / Inert atmosphere
11.1: tetrahydrofuran / 0 - 20 °C / Inert atmosphere
12.1: 40 h
With
tetrakis(triphenylphosphine) palladium(0); sodium tetrachloroaurate(III) dihyrate; 2,2'-azobis(isobutyronitrile); dimethylsulfide borane complex; iodine; tri-n-butyl-tin hydride; potassium carbonate; caesium carbonate; Dess-Martin periodane; copper(II) sulfate; sodium L-ascorbate; triethylamine; potassium hydroxide;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; benzene;
8.1: |Seyferth-Gilbert Homologation / 9.1: |Sonogashira Cross-Coupling;
DOI:10.1021/ol3027945