Total Synthesis of (R,R,R)‐γ‐Tocopherol through Cu‐Catalyzed Asymmetric 1,2‐Addition |
| |
| Authors: | Zhongtao Wu Prof?Dr Syuzanna R Harutyunyan Prof?Dr Adriaan J Minnaard |
| |
| Affiliation: | Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 7, 9747 AG, Groningen (The Netherlands) |
| |
| Abstract: | Based on the asymmetric copper‐catalyzed 1,2‐addition of Grignard reagents to ketones, (R,R,R)‐γ‐tocopherol has been synthesized in 36 % yield over 12 steps (longest linear sequence). The chiral center in the chroman ring was constructed with 73 % ee by the 1,2‐addition of a phytol‐derived Grignard reagent to an α‐bromo enone prepared from 2,3‐dimethylquinone. |
| |
| Keywords: | (R R R)‐γ ‐tocopherol 1 2‐addition asymmetric catalysis natural product synthesis vitamin E |
|
|
