Multi-step reaction with 12 steps
1.1: triethylamine / dichloromethane / 0.5 h / Cooling with ice
2.1: 4-methylmorpholine N-oxide; osmium(VIII) oxide / tetrahydrofuran; water; tert-butyl alcohol / 2 h / 20 °C
3.1: sodium periodate / tetrahydrofuran; water; tert-butyl alcohol / 1.5 h
4.1: copper(II) sulfate / dichloromethane / 16 h / 20 °C
5.1: n-butyllithium; 2,2,6,6-tetramethyl-piperidine / tetrahydrofuran; toluene / 0.5 h / 0 °C
5.2: 0.5 h / -65 - -10 °C
6.1: cesium fluoride / dimethyl sulfoxide / 15 h / 120 °C
7.1: hydrogenchloride / dichloromethane / 1 h / 25 °C
8.1: trimethyl orthoformate; sodium tris(acetoxy)borohydride / dichloromethane / 2 h / 23 °C
9.1: XPhos; tris-(dibenzylideneacetone)dipalladium(0) / tetrahydrofuran / 0.25 h / Inert atmosphere
9.2: 0.67 h / 135 °C / Inert atmosphere; Microwave irradiation
10.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h
11.1: hydrogenchloride / 1,4-dioxane; methanol / 1 h / 50 °C
12.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 20 °C
With
2,2,6,6-tetramethyl-piperidine; hydrogenchloride; sodium periodate; tris-(dibenzylideneacetone)dipalladium(0); osmium(VIII) oxide; n-butyllithium; tetrabutyl ammonium fluoride; sodium tris(acetoxy)borohydride; copper(II) sulfate; 4-methylmorpholine N-oxide; triethylamine; N-ethyl-N,N-diisopropylamine; cesium fluoride; XPhos; trimethyl orthoformate;
In
tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; dimethyl sulfoxide; toluene; tert-butyl alcohol;
DOI:10.1021/jm300118s