Multi-step reaction with 16 steps
1.1: palladium 10% on activated carbon; hydrogen / methanol / 3 h
2.1: diisobutylaluminium hydride / dichloromethane; toluene / 0.58 h / -78 °C / Inert atmosphere
3.1: dichloromethane / 84 h / 20 °C / Inert atmosphere
4.1: diisobutylaluminium hydride / dichloromethane; toluene / 0.58 h / -78 °C / Inert atmosphere
5.1: triethylamine / tetrahydrofuran / 1 h / 0 - 20 °C / Inert atmosphere
6.1: lithium bromide / tetrahydrofuran / 1 h / -10 °C / Inert atmosphere
7.1: n-butyllithium / tetrahydrofuran; hexane / 0.33 h / -78 - -10 °C / Inert atmosphere
7.2: 0.33 h / -10 - 20 °C / Inert atmosphere
8.1: dichloro [1,1'-bis(diphenylphosphino)propane]palladium(II); lithium triethylborohydride / tetrahydrofuran / 7.5 h / 0 °C / Inert atmosphere
9.1: water; scandium tris(trifluoromethanesulfonate) / acetonitrile / 74 h / 20 °C
10.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 9 h / 20 °C / Inert atmosphere
11.1: potassium hexamethylsilazane / tetrahydrofuran; toluene / 0.5 h / 0 - 20 °C / Inert atmosphere
12.1: 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate / tetrahydrofuran; toluene / 0.17 h / 20 °C / Inert atmosphere
13.1: sodium hydrogencarbonate / dichloromethane; water / 4 h / 20 °C
14.1: carbon tetrabromide; triethylamine; triphenylphosphine / dichloromethane / 0.25 h / -10 - 20 °C / Inert atmosphere
15.1: pyridine N-oxide; iodine / acetonitrile / 0.5 h / 20 °C / Inert atmosphere; Molecular sieve
16.1: acetonitrile / 1 h / 20 °C / Inert atmosphere
With
pyridine N-oxide; 2,6-dimethylpyridine; n-butyllithium; dichloro [1,1'-bis(diphenylphosphino)propane]palladium(II); carbon tetrabromide; trimethylsilyl trifluoromethanesulfonate; palladium 10% on activated carbon; water; hydrogen; iodine; potassium hexamethylsilazane; diisobutylaluminium hydride; lithium triethylborohydride; sodium hydrogencarbonate; triethylamine; triphenylphosphine; lithium bromide; scandium tris(trifluoromethanesulfonate); 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione;
In
tetrahydrofuran; methanol; hexane; dichloromethane; water; dimethyl sulfoxide; toluene; acetonitrile;
3.1: Wittig reaction / 11.1: Wittig reaction;
DOI:10.1021/ol200308m