Multi-step reaction with 9 steps
1.1: diisobutylaluminium hydride / dichloromethane; toluene / 1.5 h / -78 °C / Inert atmosphere
2.1: triethylamine / dichloromethane / 1 h / 0 °C / Inert atmosphere
3.1: osmium(VIII) oxide; water; 4-methylmorpholine N-oxide / tetrahydrofuran; tert-butyl alcohol / 6 h / 20 °C / Inert atmosphere
4.1: lead(IV) tetraacetate / benzene / 0.5 h / 20 °C / Inert atmosphere
5.1: sodium dihydrogenphosphate; sodium chlorite; 2-methyl-but-2-ene; water / tetrahydrofuran; tert-butyl alcohol / 3 h / 20 °C / Inert atmosphere
6.1: dmap; 2-methyl-6-nitrobenzoic anhydride / dichloromethane / 20 °C / Inert atmosphere
7.1: tetrahydrofuran; 1,1-Dibromoethane; N,N,N,N,-tetramethylethylenediamine; titanium tetrachloride; lead(II) chloride; zinc / dichloromethane / 2 h / 65 °C / Inert atmosphere
7.2: 16 h / 80 °C
8.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / 2 h / 20 °C / Inert atmosphere; Molecular sieve
9.1: zinc trifluoromethanesulfonate / dichloromethane / 20 °C / Inert atmosphere
With
tetrahydrofuran; dmap; sodium chlorite; sodium dihydrogenphosphate; osmium(VIII) oxide; tetrapropylammonium perruthennate; 2-methyl-but-2-ene; 1,1-Dibromoethane; N,N,N,N,-tetramethylethylenediamine; 2-methyl-6-nitrobenzoic anhydride; water; lead(IV) tetraacetate; titanium tetrachloride; zinc trifluoromethanesulfonate; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; triethylamine; lead(II) chloride; zinc;
In
tetrahydrofuran; dichloromethane; toluene; tert-butyl alcohol; benzene;
DOI:10.1021/ja200089f