Multi-step reaction with 13 steps
1.1: diethyl (2R,3R)-tartrate; titanium(IV) isopropylate; tert.-butylhydroperoxide / dichloromethane; decane / 3.82 h / Inert atmosphere; Molecular sieve
2.1: 1-methyl-1H-imidazole / toluene / 0 - 20 °C / Inert atmosphere
3.1: Br(coll)2BF4 / nitromethane / 0.25 h / Inert atmosphere; Cooling with ice
4.1: sodium hydroxide / methanol / 2 h / 20 °C / Inert atmosphere
5.1: triethylamine; sulfur trioxide pyridine complex / dimethyl sulfoxide / 8 h / 0 - 20 °C / Inert atmosphere
6.1: potassium carbonate / methanol / 16 h / 20 °C / Inert atmosphere
7.1: 2,6-dimethylpyridine / dichloromethane / 1 h / 0 °C / Inert atmosphere
8.1: Schwartz's reagent / dichloromethane / 0.5 h / 20 °C / Inert atmosphere; Darkness
8.2: 0.33 h / -78 °C / Inert atmosphere; Darkness
8.3: -78 - 20 °C / Inert atmosphere; Darkness
9.1: palladium 10% on activated carbon; hydrogen / ethanol / 2 h / 20 °C / 760.05 Torr / Inert atmosphere
10.1: 4-methylmorpholine N-oxide; tetrapropylammonium perruthennate / dichloromethane / 4 h / 0 - 20 °C / Inert atmosphere; Molecular sieve
11.1: methyllithium / tetrahydrofuran; diethyl ether / 2.5 h / -78 °C / Inert atmosphere
12.1: 4-methylmorpholine N-oxide; tetrapropylammonium perruthennate / dichloromethane / 0 - 20 °C / Molecular sieve; Inert atmosphere
13.1: methanol / 45 °C / Inert atmosphere
With
1-methyl-1H-imidazole; 2,6-dimethylpyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; Schwartz's reagent; tetrapropylammonium perruthennate; diethyl (2R,3R)-tartrate; palladium 10% on activated carbon; methyllithium; hydrogen; sulfur trioxide pyridine complex; potassium carbonate; 4-methylmorpholine N-oxide; triethylamine; sodium hydroxide;
In
tetrahydrofuran; methanol; diethyl ether; decane; nitromethane; ethanol; dichloromethane; dimethyl sulfoxide; toluene;
6.1: |Seyferth-Gilbert Homologation;
DOI:10.1016/j.tet.2013.04.041