Multi-step reaction with 9 steps
1: titanium(IV) isopropylate; tert.-butylhydroperoxide; L-(+)-diisopropyl tartrate / 2,2,4-trimethylpentane; dichloromethane / 4 h / -25 °C / Molecular sieve; Inert atmosphere
2: dimethylsulfone; sulfur trioxide pyridine complex; triethylamine / dichloromethane / 2 h / 0 - 20 °C
3: N-ethyl-N,N-diisopropylamine; lithium chloride / acetonitrile / 0 - 20 °C / Inert atmosphere
4: diisobutylaluminium hydride / hexane; dichloromethane / 0.17 h / -78 °C / Inert atmosphere
5: diisobutylaluminium hydride / hexane; dichloromethane / 0.17 h / -78 °C
6: titanium(IV) isopropylate; tert.-butylhydroperoxide; L-(+)-diisopropyl tartrate / 2,2,4-trimethylpentane; dichloromethane / 25 h / -40 - -30 °C / Molecular sieve; Inert atmosphere
7: pyridine; potassium diazodicarboxylate; acetic acid / methanol / 6 h / 40 °C / Inert atmosphere
8: sodium bis(2-methoxyethoxy)aluminium dihydride / tetrahydrofuran; toluene / 2 h / -40 - -10 °C / Inert atmosphere
9: 1H-imidazole; dmap / dichloromethane / 7 h / 0 - 20 °C / Inert atmosphere
With
pyridine; 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; L-(+)-diisopropyl tartrate; dimethylsulfone; sulfur trioxide pyridine complex; potassium diazodicarboxylate; diisobutylaluminium hydride; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; lithium chloride;
In
tetrahydrofuran; methanol; 2,2,4-trimethylpentane; hexane; dichloromethane; toluene; acetonitrile;
1: Sharpless epoxidation / 2: Parikh-Doering oxidation / 3: Horner-Wadsworth-Emmons olefination / 6: Sharpless epoxidation;
DOI:10.1021/ol201301b