Multi-step reaction with 11 steps
1.1: trifluoroacetic acid; N-iodo-succinimide / 3.5 h / 20 °C
2.1: N,N,N,N,N,N-hexamethylphosphoric triamide / copper(l) iodide / N,N-dimethyl-formamide / 20 - 80 °C
3.1: lithium hydroxide monohydrate / water; methanol / 0.5 h / 20 °C
3.2: pH 1
4.1: 4-methyl-morpholine; isobutyl chloroformate / tetrahydrofuran / 0.33 h / 0 °C
4.2: 1 h / -78 °C
5.1: Dess-Martin periodane / dichloromethane / 1.17 h / 0 - 20 °C
6.1: hydroxylamine hydrochloride; sodium acetate / methanol / 0.75 h / Reflux
7.1: N-chloro-succinimide / N,N-dimethyl-formamide / 1 h / 20 °C
8.1: triethylamine / dichloromethane / 0.53 h / 0 - 20 °C
8.2: 1 h / 80 °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; tetrahydrofuran / 20 °C
10.2: 4 h / 20 °C
11.1: methanol / acetic acid / 1,2-dichloro-ethane / 2 h / 67 °C
11.2: 20 °C
With
4-methyl-morpholine; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; N-chloro-succinimide; N-iodo-succinimide; osmium(VIII) oxide; lithium hydroxide monohydrate; hydroxylamine hydrochloride; sodium acetate; Dess-Martin periodane; 4-methylmorpholine N-oxide; triethylamine; trifluoroacetic acid; lithium chloride; isobutyl chloroformate;
copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); acetic acid;
In
tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide;