Literature DB >> 18537250

Toward the synthesis of cobyric acid. Enantioselective syntheses of completely differentiated ring D synthons.

Hui Wang1, Carlos Tassa, Peter A Jacobi.   

Abstract

Alkyne acids 11 were prepared in an enantioselective fashion from allylic ester derivatives 18 or 20 by Ireland-Claisen rearrangement, followed by Si-assisted elimination of HBr. The title compounds are attractive ring D synthons for an ongoing synthesis of cobyric acid.

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Year:  2008        PMID: 18537250      PMCID: PMC2575186          DOI: 10.1021/ol800985m

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


  6 in total

1.  Natural product synthesis and vitamin B12.

Authors:  A Eschenmoser; C E Wintner
Journal:  Science       Date:  1977-06-24       Impact factor: 47.728

2.  Unprecedented alkene stereocontrol in the Claisen rearrangement of cyclic bis-allylic esters.

Authors:  Chris McFarland; John Hutchison; Matthias C McIntosh
Journal:  Org Lett       Date:  2005-08-18       Impact factor: 6.005

3.  On the mechanism of Pd(0)-initiated coupling-cyclization of gamma-aminoalkynes.

Authors:  P A Jacobi; H Liu
Journal:  J Org Chem       Date:  2000-11-03       Impact factor: 4.354

4.  Enantioselective syntheses of ring-C precursors of vitamin B12. Substrate control. A novel Si-assisted elimination of vinyl bromides.

Authors:  Peter A Jacobi; Carlos Tassa
Journal:  Org Lett       Date:  2003-12-11       Impact factor: 6.005

5.  Copper-catalyzed coupling of amides and carbamates with vinyl halides.

Authors:  Lei Jiang; Gabriel E Job; Artis Klapars; Stephen L Buchwald
Journal:  Org Lett       Date:  2003-10-02       Impact factor: 6.005

Review 6.  Reduction of Carbonyl Compounds with Chiral Oxazaborolidine Catalysts: A New Paradigm for Enantioselective Catalysis and a Powerful New Synthetic Method.

Authors:  Elias J Corey; Christopher J Helal
Journal:  Angew Chem Int Ed Engl       Date:  1998-08-17       Impact factor: 15.336

  6 in total

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