Journal
ORGANIC LETTERS
Volume 12, Issue 3, Pages 580-583Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol9027804
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- MICINN of Spain [CTQ2008-04691]
- Ministere de la Recherche
- CNRS
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The asymmetric synthesis of the natural gamma-tocopherol metabolite (S)-gamma-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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