Literature DB >> 12489964

Double cycloisomerization as a novel and expeditious route to tricyclic heteroaromatic compounds: short and highly diastereoselective synthesis of (+/-)-tetraponerine T6.

Joseph T Kim1, Vladimir Gevorgyan.   

Abstract

[reaction: see text] Cu-Assisted double cycloisomerization of bis-alkynylpyrimidines afforded the 5-6-5 tricyclic heteroaromatic skeleton. This transformation was used as a key step in the highly diastereoselective total synthesis of (+/-)-tetraponerine T6.

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Year:  2002        PMID： 12489964      PMCID： PMC3687801          DOI： 10.1021/ol027129t

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


  4 in total

1.  Stereoelectronic control in addition of nucleophiles to an amidinium ion.

Authors:  C L Perrin; D B Young
Journal:  J Am Chem Soc       Date:  2001-05-16       Impact factor: 15.419

2.  A novel Cu-assisted cycloisomerization of alkynyl imines: efficient synthesis of pyrroles and pyrrole-containing heterocycles.

Authors:  A V Kel'in; A W Sromek; V Gevorgyan
Journal:  J Am Chem Soc       Date:  2001-03-07       Impact factor: 15.419

3.  Efficient synthesis of 2-mono- and 2,5-disubstituted furans via the CuI-catalyzed cycloisomerization of alkynyl ketones.

Authors:  Alexander V Kel'in; Vladimir Gevorgyan
Journal:  J Org Chem       Date:  2002-01-11       Impact factor: 4.354

4.  Tetraponerines, toxic alkaloids in the venom of the Neo-Guinean pseudomyrmecine antTetraponera sp.

Authors:  P Merlin; J C Braekman; D Daloze; J M Pasteels
Journal:  J Chem Ecol       Date:  1988-02       Impact factor: 2.626
  4 in total
  6 in total

1.  Copper-, Silver-, and Gold-Catalyzed Migratory Cycloisomerizations Leading to Heterocyclic Five-Membered Rings.

Authors:  Alexander S Dudnik; Natalia Chernyak; Vladimir Gevorgyan
Journal:  Aldrichimica Acta       Date:  2010       Impact factor: 3.667

2.  A novel 1,2-migration of acyloxy, phosphatyloxy, and sulfonyloxy groups in allenes: efficient synthesis of tri- and tetrasubstituted furans.

Authors:  Anna W Sromek; Alexander V Kel'in; Vladimir Gevorgyan
Journal:  Angew Chem Int Ed Engl       Date:  2004-04-19       Impact factor: 15.336

3.  Selective partial reduction of various heteroaromatic compounds with bridgehead nitrogen via Birch reduction protocol.

Authors:  Joseph T Kim; Vladimir Gevorgyan
Journal:  J Org Chem       Date:  2005-03-18       Impact factor: 4.354

4.  Highly diastereoselective approach toward (+/-)-tetraponerine T6 and analogues via the double cycloisomerization-reduction of bis-alkynylpyrimidines.

Authors:  Joseph T Kim; Jason Butt; Vladimir Gevorgyan
Journal:  J Org Chem       Date:  2004-08-20       Impact factor: 4.354

5.  Palladium-catalyzed arylation and heteroarylation of indolizines.

Authors:  Choul-Hong Park; Victoria Ryabova; Ilya V Seregin; Anna W Sromek; Vladimir Gevorgyan
Journal:  Org Lett       Date:  2004-04-01       Impact factor: 6.005

6.  Experimental and theoretical investigations into the stability of cyclic aminals.

Authors:  Edgar Sawatzky; Antonios Drakopoulos; Martin Rölz; Christoph Sotriffer; Bernd Engels; Michael Decker
Journal:  Beilstein J Org Chem       Date:  2016-10-31       Impact factor: 2.883
  6 in total

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