Multi-step reaction with 12 steps
1.1: dmap / dichloromethane / 0 - 20 °C
2.1: toluene-4-sulfonic acid / toluene / 2.5 h / Reflux
3.1: lithium hydroxide monohydrate; water / methanol / 48 h / 20 °C
4.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / acetonitrile / 20 °C / Inert atmosphere; Molecular sieve
5.1: hydroxylamine hydrochloride; sodium acetate / methanol / 4 h / Reflux
6.1: pyridine; sulfuric acid; p-toluenesulfonyl chloride / 0 - 55 °C
6.2: -10 - 0 °C
7.1: lithium aluminium tetrahydride / tetrahydrofuran / 2.5 h / 20 - 45 °C / Inert atmosphere
8.1: potassium carbonate / acetonitrile / 20 °C / Inert atmosphere
9.1: formic acid / water / 1 h / 20 °C
10.1: toluene-4-sulfonic acid / methanol; dichloromethane; water / 1 h / 20 °C / Inert atmosphere
10.2: 60 °C / Inert atmosphere
11.1: iron(III) chloride; acetic anhydride / -5 °C / Inert atmosphere
11.2: 1 h / 5 - 12 °C / Inert atmosphere
12.1: ozone / dichloromethane / 0.25 h / -78 °C / Inert atmosphere
12.2: 0.08 h / -78 - 20 °C / Inert atmosphere
With
pyridine; dmap; iron(III) chloride; lithium aluminium tetrahydride; formic acid; tetrapropylammonium perruthennate; lithium hydroxide monohydrate; sulfuric acid; hydroxylamine hydrochloride; water; sodium acetate; acetic anhydride; potassium carbonate; toluene-4-sulfonic acid; ozone; 4-methylmorpholine N-oxide; p-toluenesulfonyl chloride;
In
tetrahydrofuran; methanol; dichloromethane; water; toluene; acetonitrile;
6.1: Beckmann rearrangement / 6.2: Beckmann rearrangement;
DOI:10.1021/jo102475s