Multi-step reaction with 11 steps
1.1: ozone; oxygen / dichloromethane / 0.3 h / -78 °C
1.2: 6.5 h
2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.33 h / -42 °C
2.2: -42 - 20 °C
3.1: toluene / 16 h / Reflux
4.1: ozone; oxygen / methanol; dichloromethane / 0.2 h / -78 °C
4.2: 14 h
5.1: ammonium acetate; acetic acid / 0.5 h
6.1: dmap; N-ethyl-N,N-diisopropylamine / 24 h / Cooling
7.1: diisobutylaluminium hydride / toluene; dichloromethane / 10.5 h / 0 °C
8.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 15 h / 70 °C
9.1: tetrahydrofuran / 4 h / 0 °C
10.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 29 h / 70 °C
10.2: 4 h / 0 °C
11.1: potassium hydroxide / methanol; tetrahydrofuran / 1 h / 20 °C
With
dmap; ammonium acetate; oxygen; sodium hydride; diisobutylaluminium hydride; ozone; acetic acid; N-ethyl-N,N-diisopropylamine; potassium hydroxide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione;
In
tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; mineral oil;
DOI:10.1039/c2cc37110c