Multi-step reaction with 16 steps
1.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / acetonitrile / 12 h / Reflux
2.1: tetrahydrofuran / 1 h / -78 - 30 °C
2.2: 12 h / 20 °C
3.1: NOBSA / acetonitrile / 1.5 h / Reflux
3.2: 12 h / 60 - 70 °C
4.1: potassium carbonate / N,N-dimethyl-formamide / 12 h / 0 - 20 °C
5.1: methanol; sodium methylate / dichloromethane / 2.5 h / 20 °C
6.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C
6.2: 12 h / 20 °C
7.1: water; 4-methylmorpholine N-oxide; osmium(VIII) oxide / tetrahydrofuran / 24 h / 20 °C
8.1: sodium periodate / tetrahydrofuran; methanol; water / 2 h / 20 °C
8.2: 0.5 h / 0 - 20 °C
9.1: dmap / dichloromethane / 0.67 h / 0 - 20 °C
10.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 72 h / 70 - 80 °C
11.1: ammonium cerium (IV) nitrate / acetonitrile; water / 20 °C
12.1: boron trichloride / dichloromethane / 2 h / -70 °C
13.1: triphenylphosphine; pyridine; iodine / 12 h / 0 - 20 °C / Inert atmosphere
14.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran; acetonitrile / 2 h / 60 - 70 °C
15.1: triethylamine tris(hydrogen fluoride); N-iodo-succinimide / acetonitrile / 2 h / 0 - 20 °C
16.1: dmap; triethylamine / dichloromethane / 12 h / 20 °C
With
pyridine; methanol; dmap; sodium periodate; N-iodo-succinimide; osmium(VIII) oxide; ammonium cerium (IV) nitrate; tetrabutyl ammonium fluoride; water; iodine; sodium methylate; boron trichloride; sodium hydride; potassium carbonate; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine tris(hydrogen fluoride); triethylamine; triphenylphosphine; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione;
In
tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;