Multi-step reaction with 12 steps
1.1: 4-methyl-morpholine; isobutyl chloroformate / tetrahydrofuran / 0.33 h / 0 °C
1.2: 1 h / -78 °C
2.1: Dess-Martin periodane / dichloromethane / 1.17 h / 0 - 20 °C
3.1: triphenylphosphine / dichloromethane / 0.08 h / 0 °C
3.2: 0.33 h / 0 °C
4.1: n-butyllithium / hexane; tetrahydrofuran / 0.42 h / -78 °C
4.2: 0.08 h / 20 °C
5.1: phosphorus tribromide / dichloromethane / 0 - 20 °C
6.1: potassium carbonate / N,N-dimethyl-formamide / 3 h / 20 °C
7.1: hydroxylamine hydrochloride; sodium acetate / methanol / 0.5 h / Reflux
8.1: triethylamine; sodium hypochlorite / dichloromethane / 2 h / 0 - 20 °C
9.1: lithium chloride / tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane / 100 °C / Sealed tube; Inert atmosphere
10.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / water / 5 h / 20 °C
11.1: sodium periodate / water / 1 h / 20 °C
12.1: methanol / titanium(IV)isopropoxide; acetic acid / dichloromethane / 1.5 h / 20 °C
12.2: 2 h / 20 °C
With
4-methyl-morpholine; methanol; sodium hypochlorite; sodium periodate; osmium(VIII) oxide; n-butyllithium; hydroxylamine hydrochloride; sodium acetate; phosphorus tribromide; potassium carbonate; Dess-Martin periodane; 4-methylmorpholine N-oxide; triethylamine; triphenylphosphine; lithium chloride; isobutyl chloroformate;
tetrakis(triphenylphosphine) palladium(0); titanium(IV)isopropoxide; acetic acid;
In
tetrahydrofuran; 1,4-dioxane; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide;