Multi-step reaction with 12 steps
1: lithium triethylborohydride / tetrahydrofuran / 6.25 h / 20 - 45 °C / Inert atmosphere
2: boron trifluoride diethyl etherate / dichloromethane / 0.67 h / 0 - 20 °C / Inert atmosphere
3: 4-methyl-morpholine / dichloromethane / 2 h / 20 °C / Inert atmosphere
4: methyl iodide; sodium hydrogencarbonate / acetonitrile; water / 24 h / 20 °C
5: samarium diiodide / acetonitrile; methanol / 1 h / -20 °C / Inert atmosphere
6: Dess-Martin periodane / dichloromethane / 1.5 h / 20 °C / Inert atmosphere
7: sodium tetrahydroborate / dichloromethane; methanol / 0.5 h / -80 °C / Inert atmosphere
8: 2,6-dimethylpyridine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere
9: potassium hexamethylsilazane / tetrahydrofuran; toluene / 0.5 h / 0 °C / Inert atmosphere
10: diisobutylaluminium hydride / dichloromethane; hexane / 0.75 h / -80 °C / Inert atmosphere
11: lithium chloride; triethylamine / acetonitrile / 5 h / 20 °C / Inert atmosphere
12: potassium tert-butylate; tert.-butylhydroperoxide / tetrahydrofuran / 16 h / -80 - -25 °C / Inert atmosphere
With
4-methyl-morpholine; 2,6-dimethylpyridine; tert.-butylhydroperoxide; sodium tetrahydroborate; samarium diiodide; boron trifluoride diethyl etherate; potassium tert-butylate; potassium hexamethylsilazane; diisobutylaluminium hydride; lithium triethylborohydride; sodium hydrogencarbonate; Dess-Martin periodane; triethylamine; lithium chloride; methyl iodide;
In
tetrahydrofuran; methanol; hexane; dichloromethane; water; toluene; acetonitrile;
6: |Dess-Martin Oxidation / 11: |Horner-Wadsworth-Emmons Olefination;
DOI:10.1021/ol500788c