Multi-step reaction with 11 steps
1: iron; acetic acid / tetrahydrofuran; methanol / 3.5 h / 20 °C / Inert atmosphere
2: acetic acid / chloroform / 12 h / 20 °C / Molecular sieve; Inert atmosphere
3: sodium cyanoborohydride / tetrahydrofuran / 2 h / Inert atmosphere
4: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 0 °C / Inert atmosphere
5: dmap; potassium carbonate / dichloromethane / 20 °C / Inert atmosphere
6: 1,4-diaza-bicyclo[2.2.2]octane; bis(1,5-cyclooctadiene)diiridium(I) dichloride; (3,5-dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-(1-phenyl-ethyl)-amine / tetrahydrofuran / 20 °C / Inert atmosphere
7: palladium diacetate; silver nitrate; triphenylphosphine / 1,4-dioxane / 1 h / 80 °C / Inert atmosphere
8: 4-methyl-morpholine; osmium(VIII) oxide / tetrahydrofuran; water; acetone / 3 h / 20 °C / Inert atmosphere
9: pyridine / dichloromethane / 0.08 h / -78 - 0 °C / Inert atmosphere
10: tetrahydrofuran / 24 h / -20 - 0 °C / Inert atmosphere
11: methanol; sodium methylate / tetrahydrofuran / 78 °C / Inert atmosphere
With
4-methyl-morpholine; pyridine; 1,4-diaza-bicyclo[2.2.2]octane; methanol; dmap; osmium(VIII) oxide; bis(1,5-cyclooctadiene)diiridium(I) dichloride; tetrabutyl ammonium fluoride; sodium methylate; palladium diacetate; iron; sodium cyanoborohydride; potassium carbonate; silver nitrate; acetic acid; triphenylphosphine; (3,5-dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-(1-phenyl-ethyl)-amine;
In
tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; chloroform; water; acetone;
9: Polonovski reaction;
DOI:10.1002/chem.201003489