Multi-step reaction with 16 steps
1.1: dmap / toluene / 3 h / 20 °C / Inert atmosphere
2.1: palladium 10% on activated carbon; hydrogen / methanol
3.1: 4-methylmorpholine N-oxide; tetrapropylammonium perruthennate / dichloromethane / 2 h / 20 °C / Molecular sieve; Inert atmosphere
4.1: dicyclohexylboron chloride; N,N-dimethyl-ethanamine / diethyl ether; hexane / 1.5 h / 0 °C / Inert atmosphere
4.2: 26 h / -78 - -20 °C / Inert atmosphere
5.1: t-butyldimethylsiyl triflate / dichloromethane / 2 h / -50 °C / Inert atmosphere
6.1: potassium carbonate / methanol / 2 h / 20 °C / Inert atmosphere
6.2: 16 h / 20 °C / Inert atmosphere
7.1: N-ethyl-N,N-diisopropylamine; HATU / dichloromethane / 0.08 h / Inert atmosphere
7.2: 20 °C / Inert atmosphere
8.1: 2,6-dimethylpyridine; t-butyldimethylsiyl triflate / dichloromethane / 1 h / 20 °C / Inert atmosphere
9.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere
10.1: N-ethyl-N,N-diisopropylamine / dichloromethane; tetrahydrofuran / 1 h / 0 - 20 °C / Inert atmosphere
11.1: dmap; pyridine / dichloromethane / 1.08 h / 0 - 20 °C / Inert atmosphere
12.1: Triphenylphosphine oxide; trifluoromethylsulfonic anhydride / dichloromethane / 1 h / 0 °C / Inert atmosphere
13.1: ammonium acetate; zinc / water; tetrahydrofuran / 24 h / 20 °C / Inert atmosphere
14.1: N-methylaniline; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere
15.1: N-ethyl-N,N-diisopropylamine; HATU / dichloromethane / Inert atmosphere
16.1: N-methylaniline; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere
With
pyridine; 2,6-dimethylpyridine; dmap; tetrakis(triphenylphosphine) palladium(0); tetrapropylammonium perruthennate; N,N-dimethyl-ethanamine; trifluoromethylsulfonic anhydride; palladium 10% on activated carbon; t-butyldimethylsiyl triflate; dicyclohexylboron chloride; ammonium acetate; tetrabutyl ammonium fluoride; hydrogen; potassium carbonate; 4-methylmorpholine N-oxide; N-ethyl-N,N-diisopropylamine; HATU; N-methylaniline; Triphenylphosphine oxide; zinc;
In
tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; toluene;
DOI:10.1021/ol302309c