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Enantioselective Total Synthesis of the Natural γ-Tocopherol Metabolite (S)-γ-CEHC [(S)-LLU-α]

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journal contribution
posted on 05.02.2010, 00:00 by Mercedes Lecea, Gloria Hernández-Torres, Antonio Urbano, M. Carmen Carreño, Françoise Colobert
The asymmetric synthesis of the natural γ-tocopherol metabolite (S)-γ-CEHC (1) is described in 10 steps and 18.4% overall yield starting from 2,3-dimethylhydroquinone. The key step is a stereoselective TiCl4-mediated homochiral sulfoxide-directed allylation of ketal (SS)-3 to efficiently generate the challenging C-2 stereogenic carbon of chroman (SS,S)-2 with the correct absolute configuration.

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