Literature DB >> 14682745

Studies on the synthesis of gymnodimine. construction of the spiroimine portion via Diels-Alder cycloaddition.

James D White1, Guoqiang Wang, Laura Quaranta.   

Abstract

An azaspiro[5.5]undecadiene corresponding to a subunit of the shellfish toxin gymnodimine was synthesized by Diels-Alder cycloaddition. One member of the pair of stereoisomeric adducts was transformed to a spiroimine, which will serve as the core around which the macrocyclic portion of the toxin will be assembled. [structure: see text]

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Year:  2003        PMID： 14682745     DOI： 10.1021/ol035939e

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


  4 in total

Review 1.  Synthesis and biology of cyclic imine toxins, an emerging class of potent, globally distributed marine toxins.

Authors:  Craig E Stivala; Evelyne Benoit; Rómulo Aráoz; Denis Servent; Alexei Novikov; Jordi Molgó; Armen Zakarian
Journal:  Nat Prod Rep       Date:  2015-03       Impact factor: 13.423

2.  Total synthesis of the spirocyclic imine marine toxin (-)-gymnodimine and an unnatural C4-epimer.

Authors:  Ke Kong; Ziad Moussa; Changsuk Lee; Daniel Romo
Journal:  J Am Chem Soc       Date:  2011-11-16       Impact factor: 15.419

3.  Highly Selective Dopamine D3 Receptor (D3R) Antagonists and Partial Agonists Based on Eticlopride and the D3R Crystal Structure: New Leads for Opioid Dependence Treatment.

Authors:  Vivek Kumar; Alessandro Bonifazi; Michael P Ellenberger; Thomas M Keck; Elie Pommier; Rana Rais; Barbara S Slusher; Eliot Gardner; Zhi-Bing You; Zheng-Xiong Xi; Amy Hauck Newman
Journal:  J Med Chem       Date:  2016-08-10       Impact factor: 7.446

4.  Enantioselective total synthesis of the marine toxin (-)-gymnodimine employing a Barbier-type macrocyclization.

Authors:  Ke Kong; Daniel Romo; Changsuk Lee
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336
  4 in total

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