Multi-step reaction with 13 steps
1.1: n-butyllithium / tetrahydrofuran / 1 h / -78 °C
1.2: 3 h / -78 - -40 °C
2.1: acetic acid / 100 °C / sealed tube
3.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 45 °C
4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1 h / 20 °C
5.1: N-iodo-succinimide / acetonitrile / 1 h / 20 °C
6.1: potassium phosphate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane; water / 90 °C / Inert atmosphere
7.1: N-Bromosuccinimide / acetonitrile / 0.5 h / 20 °C
8.1: tetrakis(triphenylphosphine) palladium(0) / acetonitrile / 1 h / 150 °C / microwave irradiation
9.1: 2,6-dimethylpyridine; sodium periodate / osmium(VIII) oxide / 1,4-dioxane; water / 96 h / 20 °C
10.1: sodium tetrahydroborate; methanol / 1 h / 20 °C
11.1: triethylamine; methanesulfonyl chloride / tetrahydrofuran / 1 h / 0 - 20 °C
11.2: 20 °C
12.1: trifluoroacetic acid / water / 1 h
13.1: pyridine / 20 °C
With
pyridine; 2,6-dimethylpyridine; methanol; sodium tetrahydroborate; potassium phosphate; sodium periodate; N-Bromosuccinimide; N-iodo-succinimide; n-butyllithium; acetic acid; methanesulfonyl chloride; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid;
osmium(VIII) oxide; tetrakis(triphenylphosphine) palladium(0); dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2;
In
tetrahydrofuran; 1,4-dioxane; dichloromethane; water; acetonitrile;