Multi-step reaction with 10 steps
1.1: sulfur trioxide pyridine complex; triethylamine / dichloromethane; dimethyl sulfoxide / 3 h / 0 °C / Inert atmosphere
2.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -20 °C / Inert atmosphere
2.2: -78 °C / Inert atmosphere
3.1: sodium hydride / tetrahydrofuran; N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C / Inert atmosphere
3.2: 4 h / 0 °C / Inert atmosphere
4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere
5.1: sulfur trioxide pyridine complex; triethylamine / dichloromethane; dimethyl sulfoxide / 2 h / 0 °C / Inert atmosphere
6.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere
6.2: 0 °C / Inert atmosphere
7.1: water; calcium carbonate; methyl iodide / acetonitrile / 24 h / 40 °C / Inert atmosphere
8.1: dichloromethane / 15 h / -78 - 20 °C / Inert atmosphere
9.1: dihydrogen peroxide / methanol; dichloromethane; water / 1 h / 0 °C / Inert atmosphere
10.1: Inert atmosphere
With
n-butyllithium; tetrabutyl ammonium fluoride; water; dihydrogen peroxide; sodium hexamethyldisilazane; sulfur trioxide pyridine complex; sodium hydride; triethylamine; calcium carbonate; methyl iodide;
In
tetrahydrofuran; methanol; hexane; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile; mineral oil;
6.2: Wittig reaction / 8.1: Aldol condensation;
DOI:10.1021/ol2007296