Enantioselective total synthesis of the natural γ -tocopherol metabolite (S)-γ-CEHC (S)-LLU-α
[Chemical equation presented] The asymmetric synthesis of the natural: -tocopherol metabolite (S)-; -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.
Lecea, Mercedes,Hernandez-Torres, Gloria,Urbano, Antonio,Carreno, M. Carmen,Colobert, Francoise
supporting information; experimental part
p. 580 - 583
(2010/05/18)
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