Multi-step reaction with 14 steps
1.1: n-butyllithium / hexane; tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere
1.2: 1.5 h / 0 °C / Inert atmosphere
2.1: selenium(IV) oxide; tert.-butylhydroperoxide / dichloromethane; water / 16 h / 20 °C / Inert atmosphere
3.1: [Rh(nbd)(diphos-4)]BF4; hydrogen / tetrahydrofuran / 2 h / 20 °C / 31029.7 Torr
4.1: 2,6-dimethylpyridine / dichloromethane / 1 h / -78 °C / Inert atmosphere
5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 6.33 h / 0 - 20 °C / Inert atmosphere
6.1: Dess-Martin periodane; sodium hydrogencarbonate / dichloromethane / 1.5 h / 0 - 20 °C / Inert atmosphere
7.1: trimethylphosphane; titanium(IV) isopropylate / tetrahydrofuran / 3 h / 70 °C / Inert atmosphere
8.1: cerium(III) chloride heptahydrate / tetrahydrofuran / 0.25 h / 20 °C / Schlenk technique; Inert atmosphere
8.2: 0.25 h / 0 °C / Schlenk technique; Inert atmosphere
9.1: titanium tetrachloride / dichloromethane; toluene / 0.25 h / 0 °C / Inert atmosphere
9.2: 0.5 h / -78 °C / Inert atmosphere
10.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 36 h / 65 °C / Inert atmosphere
11.1: hydrogen; palladium 10% on activated carbon / methanol / 5 h
12.1: Dess-Martin periodane; sodium hydrogencarbonate / dichloromethane / 1.5 h / 0 - 20 °C / Inert atmosphere
13.1: titanium tetrachloride; magnesium / dichloromethane; tetrahydrofuran / 6 h / Inert atmosphere; Reflux
14.1: silver(II) oxide; nitric acid / 1,4-dioxane / 0.25 h / 20 °C / Inert atmosphere
With
2,6-dimethylpyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; selenium(IV) oxide; silver(II) oxide; n-butyllithium; cerium(III) chloride heptahydrate; palladium 10% on activated carbon; [Rh(nbd)(diphos-4)]BF4; tetrabutyl ammonium fluoride; hydrogen; nitric acid; titanium tetrachloride; sodium hydrogencarbonate; Dess-Martin periodane; magnesium; trimethylphosphane;
In
tetrahydrofuran; 1,4-dioxane; methanol; hexane; dichloromethane; water; toluene;
1.1: |Wittig Olefination / 1.2: |Wittig Olefination;
DOI:10.1021/ja413106t