Multi-step reaction with 9 steps
1.1: diisopropylamine; n-butyllithium / hexane; tetrahydrofuran / 18.75 h / -78 - -30 °C
1.2: 20 °C
2.1: sodium azide / N,N-dimethyl-formamide / 18 h / 20 °C
3.1: triethylamine; titanium tetrachloride / dichloromethane / 0 - 20 °C / Inert atmosphere
4.1: toluene / 2 h / 105 °C
5.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 5 h / 0 - 20 °C
6.1: triethylamine / 1,1'-bis(diphenylphosphino)ferrocenedichloropalladium (II) chloroform / propan-1-ol / 1.5 h / 100 °C
7.1: phosphorus(V) oxybromide / dichloromethane / 1.5 h / 0 - 20 °C / Inert atmosphere
8.1: caesium carbonate / 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 80 °C / Inert atmosphere; Sealed tube
9.1: osmium(VIII) oxide; sodium periodate / water; tert-butyl alcohol; acetone / 20 °C
With
sodium periodate; osmium(VIII) oxide; n-butyllithium; sodium azide; titanium tetrachloride; caesium carbonate; triethylamine; diisopropylamine; 3-chloro-benzenecarboperoxoic acid; phosphorus(V) oxybromide;
tris-(dibenzylideneacetone)dipalladium(0); 1,1'-bis(diphenylphosphino)ferrocenedichloropalladium (II) chloroform; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene;
In
tetrahydrofuran; 1,4-dioxane; propan-1-ol; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; tert-butyl alcohol;