Multi-step reaction with 11 steps
1.1: tetrahydrofuran / 12 h / 65 °C
2.1: diisobutylaluminium hydride / toluene / 2 h / -78 °C / Inert atmosphere
3.1: di-isopropyl azodicarboxylate; triphenylphosphine / toluene / -10 °C / Inert atmosphere
4.1: sodium; methanol / 1 h / 0 - 20 °C / Inert atmosphere
5.1: pyridine / 72 h / 110 °C
6.1: potassium carbonate; palladium 10% on activated carbon; hydrogen / ethyl acetate / 48 h / 20 °C / 760.05 Torr
7.1: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere
8.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / 0 °C / Inert atmosphere
8.2: 0 - 20 °C / Inert atmosphere
9.1: acetic acid / methanol / 48 h / 20 °C
10.1: water; sodium hydroxide; tetra-(n-butyl)ammonium iodide / toluene / 48 h / 45 °C
10.2: 1 h / 0 °C / Inert atmosphere
10.3: 12 h / 0 - 20 °C / Inert atmosphere
11.1: water; osmium(VIII) oxide; 4-methylmorpholine N-oxide / acetone; tert-butyl alcohol / 24 h / 0 - 20 °C
With
pyridine; methanol; osmium(VIII) oxide; lithium aluminium tetrahydride; di-isopropyl azodicarboxylate; palladium 10% on activated carbon; water; hydrogen; sodium; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; potassium carbonate; acetic acid; 4-methylmorpholine N-oxide; triphenylphosphine; sodium hydroxide;
In
tetrahydrofuran; methanol; ethyl acetate; N,N-dimethyl-formamide; acetone; toluene; mineral oil; tert-butyl alcohol;
3.1: |Mitsunobu Displacement / 8.2: |Williamson Ether Synthesis / 10.3: |Williamson Ether Synthesis;
DOI:10.1055/s-0032-1317929