Multi-step reaction with 14 steps
1: silver(l) oxide / N,N-dimethyl-formamide / 24 h / 20 °C
2: ammonium cerium (IV) nitrate / water; acetonitrile / 2.5 h / 0 - 20 °C
3: dmap; triethylamine / dichloromethane / 2 h / 0 °C
4: tetrahydrofuran / 1.5 h / -78 °C
5: sodium tetrahydroborate; cerium(III) chloride heptahydrate / methanol / 2 h / 0 °C
6: pyridine / 12 h / 0 - 20 °C
7: tetrakis(triphenylphosphine) palladium(0); ammonium formate; triethylamine / toluene / 0.5 h / Reflux
8: osmium(VIII) oxide; 4-methylmorpholine N-oxide / water; acetone; tert-butyl alcohol / 24 h / 20 °C
9: sodium periodate / tetrahydrofuran; water / 3.5 h / 0 - 20 °C
10: t-butyldimethylsiyl triflate / toluene / 9 h / -78 °C
11: osmium(VIII) oxide; 4-methylmorpholine N-oxide / water; acetone; tert-butyl alcohol / 24 h / 20 °C
12: sodium periodate / tetrahydrofuran; water / 4 h / 0 - 20 °C
13: tetrahydrofuran / 4.5 h / -78 - 0 °C / Inert atmosphere
14: hydrogenchloride / methanol; water / 12 h / 20 °C
With
pyridine; hydrogenchloride; dmap; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; tetrakis(triphenylphosphine) palladium(0); ammonium cerium (IV) nitrate; cerium(III) chloride heptahydrate; t-butyldimethylsiyl triflate; ammonium formate; 4-methylmorpholine N-oxide; triethylamine; silver(l) oxide;
In
tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; tert-butyl alcohol;
DOI:10.1016/j.tetlet.2011.01.018