Literature DB >> 16356009

Stereocontrolled synthesis of (-)-kainic acid from trans-4-hydroxy-L-proline.

Jean-François Poisson1, Arturo Orellana, Andrew E Greene.   

Abstract

[reaction: see text] A highly stereoselective synthesis of (-)-kainic acid has been achieved in 14 steps and >7% overall yield starting from inexpensive trans-4-hydroxy-L-proline. The key steps are diastereoselective enolate alkylation and cuprate substitution reactions.

Entities:  

Year:  2005        PMID： 16356009     DOI： 10.1021/jo051508t

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  3 in total

1.  Total Syntheses of the Reported Structures of Curcusones I and J through Tandem Gold Catalysis.

Authors:  Yong Li; Mingji Dai
Journal:  Angew Chem Int Ed Engl       Date:  2017-08-10       Impact factor: 15.336

Review 2.  The 9-phenyl-9-fluorenyl group for nitrogen protection in enantiospecific synthesis.

Authors:  Essi J Karppanen; Ari M P Koskinen
Journal:  Molecules       Date:  2010-09-17       Impact factor: 4.411

3.  2-Ketoglutarate-Generated In Vitro Enzymatic Biosystem Facilitates Fe(II)/2-Ketoglutarate-Dependent Dioxygenase-Mediated C-H Bond Oxidation for (2s,3r,4s)-4-Hydroxyisoleucine Synthesis.

Authors:  Xiao-Ran Jing; Huan Liu; Yao Nie; Yan Xu
Journal:  Int J Mol Sci       Date:  2020-07-28       Impact factor: 5.923
  3 in total

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