Literature DB >> 20052974

Enantioselective total synthesis of the natural gamma-tocopherol metabolite (S)-gamma-CEHC [(S)-LLU-alpha].

Mercedes Lecea1, Gloria Hernández-Torres, Antonio Urbano, M Carmen Carreño, Françoise Colobert.   

Abstract

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 TiCl(4)-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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Year:  2010        PMID： 20052974     DOI： 10.1021/ol9027804

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  4 in total

1.  Synthesis of (2R,8' S,3' E)-δ-tocodienol, a tocoflexol family member designed to have a superior pharmacokinetic profile compared to δ-tocotrienol.

Authors:  Xingui Liu; Satheesh Gujarathi; Xuan Zhang; Lijian Shao; Marjan Boerma; Cesar M Compadre; Peter A Crooks; Martin Hauer-Jensen; Daohong Zhou; Guangrong Zheng
Journal:  Tetrahedron       Date:  2016-05-12       Impact factor: 2.457

2.  5,6-Dimethyl-1,2,9,10-tetra-hydro-pyrano[3,2-f]chromene-3,8-dione.

Authors:  Shailesh K Goswami; Lyall R Hanton; C John McAdam; Stephen C Moratti; Jim Simpson
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-06-27

3.  6-Hy-droxy-7,8-dimethyl-chroman-2-one.

Authors:  Shailesh K Goswami; Lyall R Hanton; C John McAdam; Stephen C Moratti; Jim Simpson
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-07-04

4.  Concise Synthesis of (S)-δ-CEHC, a Metabolite of Vitamin E.

Authors:  Matthew Burke; Pratik Pal; Peiyi Zhang; Xuan Zhang; Guangrong Zheng
Journal:  ACS Omega       Date:  2021-02-02
  4 in total

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