Multi-step reaction with 18 steps
1: 1H-imidazole; iodine; triphenylphosphine / toluene / 20 h / 20 °C
2: N,N,N,N,N,N-hexamethylphosphoric triamide; copper(l) iodide / tetrahydrofuran / 4 h / -40 - 20 °C
3: osmium(VIII) oxide; water; 4-methylmorpholine N-oxide / acetone / 72 h / 20 °C
4: sodium periodate / tetrahydrofuran; water / 0.5 h / 0 - 20 °C
5: zinc trifluoromethanesulfonate; triethylamine / toluene / 48 h / 20 - 60 °C
6: methanol; potassium carbonate / 15 h / 20 °C
7: lithium aluminium tetrahydride / tetrahydrofuran / 0.5 h / 0 °C
8: 1H-imidazole / dichloromethane / 5 h / 0 - 20 °C
9: osmium(VIII) oxide; water; 4-methylmorpholine N-oxide / acetone / 120 h / 20 °C
10: N-iodo-succinimide; triphenylphosphine / tetrahydrofuran / 3 h / 0 - 20 °C
11: N,N,N,N,N,N-hexamethylphosphoric triamide; copper(l) iodide / tetrahydrofuran / 7 h / -40 - 20 °C
12: toluene-4-sulfonic acid / dichloromethane / 8 h / 0 - 20 °C
13: tetrabutyl ammonium fluoride / tetrahydrofuran / 10 h / 0 - 20 °C
14: dmap; triethylamine / dichloromethane / 168 h / 0 - 20 °C
15: methanol; toluene-4-sulfonic acid / 24 h / 20 °C
16: potassium carbonate / methanol / 5 h / 20 °C
17: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 0 - 20 °C
18: AD-mix-β; water / tert-butyl alcohol / 48 h / 0 °C
With
1H-imidazole; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; sodium periodate; N-iodo-succinimide; copper(l) iodide; osmium(VIII) oxide; lithium aluminium tetrahydride; AD-mix-β; tetrabutyl ammonium fluoride; water; iodine; zinc trifluoromethanesulfonate; potassium carbonate; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine;
In
tetrahydrofuran; methanol; dichloromethane; water; acetone; toluene; tert-butyl alcohol;
5: Carreira's addition / 18: Sharpless asymmetric dihydroxylation;
DOI:10.1016/j.tetlet.2012.02.090