Multi-step reaction with 9 steps
1.1: Inert atmosphere
2.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.25 h / 0 - 20 °C / Inert atmosphere
2.2: 20 °C / Inert atmosphere
3.1: C46H51O5P; chloro(1,5-cyclooctadiene)rhodium(I) dimer; silver tetrafluoroborate; triethylamine / tetrahydrofuran / 12 h / 20 °C / Inert atmosphere
4.1: tetrahydrofuran / -78 - 20 °C / Inert atmosphere
4.2: 2 h / -78 °C / Inert atmosphere
4.3: 2 h / -78 - 20 °C / Inert atmosphere
5.1: tetrabutyl ammonium fluoride; water / tetrahydrofuran / 0 - 20 °C / Inert atmosphere
6.1: N-ethyl-N,N-diisopropylamine; sulfur trioxide pyridine complex; dimethyl sulfoxide / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere
7.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / 0 - 20 °C / Inert atmosphere
7.2: 24 h / -78 - 20 °C / Inert atmosphere
8.1: Lawessons reagent / toluene / 6 h / Inert atmosphere; Reflux
9.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere
9.2: 9 h / -78 - 20 °C / Inert atmosphere
With
Lawessons reagent; silver tetrafluoroborate; chloro(1,5-cyclooctadiene)rhodium(I) dimer; n-butyllithium; C46H51O5P; tetrabutyl ammonium fluoride; water; sodium hexamethyldisilazane; sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine;
In
tetrahydrofuran; hexane; dichloromethane; toluene;
6.1: |Parikh-Doering Oxidation / 7.1: |Wittig Olefination / 7.2: |Wittig Olefination;
DOI:10.1021/jacs.7b02324