Multi-step reaction with 13 steps
1.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / ethyl acetate / 20 h / 65 °C / Inert atmosphere
2.1: sodium acetate; acetic acid / 12 h / 80 °C / Inert atmosphere
3.1: hydrogenchloride; water / methanol; tetrahydrofuran / 16 h / 50 °C
4.1: toluene-4-sulfonic acid / acetone / 0.33 h / Inert atmosphere
4.2: 0.33 h
5.1: triethylamine; dmap / dichloromethane / 2 h / 0 °C / Inert atmosphere
6.1: hydrogenchloride; water / methanol; tetrahydrofuran / 16 h / 50 °C
7.1: methanesulfonyl chloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 0 °C / Inert atmosphere
7.2: 1 h / 0 °C / Inert atmosphere
8.1: ammonium cerium (IV) nitrate / water; ethyl acetate; acetonitrile / 1.25 h / 0 °C
9.1: toluene / 12 h / 100 °C / Schlenk technique; Inert atmosphere
10.1: Jones reagent; potassium fluoride / acetone / 45 h / 0 °C / Inert atmosphere
11.1: triethylamine / 0.17 h / Inert atmosphere
12.1: dmap; pyridine / dichloromethane / 16 h / 0 - 20 °C / Inert atmosphere
13.1: bis(tri-t-butylphosphine)palladium(0) / toluene / 0.25 h / 80 °C / Inert atmosphere
With
pyridine; hydrogenchloride; dmap; potassium fluoride; Jones reagent; ammonium cerium (IV) nitrate; bis(tri-t-butylphosphine)palladium(0); water; sodium acetate; toluene-4-sulfonic acid; acetic acid; methanesulfonyl chloride; triethylamine; N-ethyl-N,N-diisopropylamine; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione;
In
tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; acetone; toluene; acetonitrile;
9.1: |Diels-Alder Cycloaddition / 13.1: |Stille Cross Coupling;
DOI:10.1002/chem.201402254