Multi-step reaction with 12 steps
1.1: (DHQD)2PHAL; methanesulfonamide; potassium osmate(VI) dihydrate; potassium hexacyanoferrate(III); potassium carbonate; sodium hydrogencarbonate / tert-butyl alcohol; water / 4 h / 0 °C / Inert atmosphere
2.1: sodium hydroxide / tetrahydrofuran / 2 h / 0 °C / Inert atmosphere
3.1: 1H-imidazole / dichloromethane / 14 h / 0 - 20 °C / Inert atmosphere
4.1: copper(l) iodide / tetrahydrofuran; diethyl ether / 1 h / -78 - 20 °C / Inert atmosphere
5.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 6 h / 40 °C / Inert atmosphere
6.1: tris(dibenzylideneacetone)dipalladium(0) chloroform complex; trans-1,2-(1S,2S)-1,2-diaminocyclohexane-N,N’-bis(2’-diphenylphosphinobenzoyl) / tetrahydrofuran / 50 °C / Inert atmosphere
7.1: triethylamine / methanol / 0.75 h / 20 °C / Inert atmosphere
8.1: magnesium bromide / diethyl ether / 16 h / 0 - 20 °C / Inert atmosphere
9.1: 2,6-dimethylpyridine / dichloromethane / 2 h / 0 °C / Inert atmosphere
10.1: dimethylsulfide borane complex / tetrahydrofuran / 4 h / 0 - 20 °C / Inert atmosphere
10.2: 1 h / 0 °C / Inert atmosphere
11.1: Dess-Martin periodane; sodium hydrogencarbonate / dichloromethane / 0.5 h / 0 - 20 °C / Inert atmosphere
12.1: sec.-butyllithium / tetrahydrofuran; cyclohexane / 0.5 h / -78 °C / Inert atmosphere
12.2: 4 h / -78 - 20 °C / Inert atmosphere
12.3: 0.5 h / 0 °C / Inert atmosphere
With
(DHQD)2PHAL; 1H-imidazole; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; 2,6-dimethylpyridine; trans-1,2-(1S,2S)-1,2-diaminocyclohexane-N,N’-bis(2’-diphenylphosphinobenzoyl); tris(dibenzylideneacetone)dipalladium(0) chloroform complex; potassium osmate(VI) dihydrate; copper(l) iodide; methanesulfonamide; dimethylsulfide borane complex; sec.-butyllithium; sodium hydrogencarbonate; potassium carbonate; Dess-Martin periodane; triethylamine; sodium hydroxide; magnesium bromide; potassium hexacyanoferrate(III);
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; cyclohexane; water; tert-butyl alcohol;
1.1: |Sharpless Dihydroxylation;
DOI:10.1021/ol302409g