Literature DB >> 21058673

Palladium-catalyzed intramolecular carbopalladation/cyclization cascade: access to polycyclic N-fused heterocycles.

Dmitri Chernyak1, Vladimir Gevorgyan.   

Abstract

An efficient palladium-catalyzed intramolecular carbopalladation/cyclization cascade toward tetra- and pentacyclic N-fused heterocycles has been developed. This transformation proceeds via the palladium-catalyzed coupling of aryl halides with internal propargylic esters or ethers followed by the 5-endo-dig cyclization leading to polycyclic pyrroloheterocycles in moderate to excellent yields.

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Year:  2010        PMID： 21058673      PMCID： PMC3131228          DOI： 10.1021/ol102447s

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


  25 in total

1.  Gold-catalyzed 1,2-migration of silicon, tin, and germanium en route to C-2 substituted fused pyrrole-containing heterocycles.

Authors:  Ilya V Seregin; Vladimir Gevorgyan
Journal:  J Am Chem Soc       Date:  2006-09-20       Impact factor: 15.419

2.  Synthesis and structure-activity relationship study of potent cytotoxic analogues of the marine alkaloid Lamellarin D.

Authors:  Daniel Pla; Antonio Marchal; Christian A Olsen; Andrés Francesch; Carmen Cuevas; Fernando Albericio; Mercedes Alvarez
Journal:  J Med Chem       Date:  2006-06-01       Impact factor: 7.446

3.  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

4.  Inhibition of mitochondrial respiration mediates apoptosis induced by the anti-tumoral alkaloid lamellarin D.

Authors:  Caroline Ballot; Jérome Kluza; Steve Lancel; Alain Martoriati; Sidi Mohamed Hassoun; Laurent Mortier; Jean-Claude Vienne; Gilbert Briand; Pierre Formstecher; Christian Bailly; Remi Nevière; Philippe Marchetti
Journal:  Apoptosis       Date:  2010-07       Impact factor: 4.677

5.  Total synthesis of natural and unnatural lamellarins with saturated and unsaturated D-rings.

Authors:  Poonsakdi Ploypradith; Thaninee Petchmanee; Poolsak Sahakitpichan; Nichole D Litvinas; Somsak Ruchirawat
Journal:  J Org Chem       Date:  2006-12-08       Impact factor: 4.354

6.  Molecular determinants of topoisomerase I poisoning by lamellarins: comparison with camptothecin and structure-activity relationships.

Authors:  Esther Marco; William Laine; Christelle Tardy; Amélie Lansiaux; Masatomo Iwao; Fumito Ishibashi; Christian Bailly; Federico Gago
Journal:  J Med Chem       Date:  2005-06-02       Impact factor: 7.446

7.  Multisubstituted N-fused heterocycles via transition metal-catalyzed cycloisomerization protocols.

Authors:  Ilya V Seregin; Alex W Schammel; Vladimir Gevorgyan
Journal:  Tetrahedron       Date:  2008-07-14       Impact factor: 2.457

8.  Mechanistically diverse copper-, silver-, and gold-catalyzed acyloxy and phosphatyloxy migrations: efficient synthesis of heterocycles via cascade migration/cycloisomerization approach.

Authors:  Todd Schwier; Anna W Sromek; Dahrika M L Yap; Dmitri Chernyak; Vladimir Gevorgyan
Journal:  J Am Chem Soc       Date:  2007-07-21       Impact factor: 15.419

9.  Lamellarin D bioconjugates I: Synthesis and cellular internalization of PEG-derivatives.

Authors:  Daniel Pla; Andrés Francesch; Pilar Calvo; Carmen Cuevas; Rosa Aligué; Fernando Albericio; Mercedes Alvarez
Journal:  Bioconjug Chem       Date:  2009-06       Impact factor: 4.774

10.  TBDPS and Br-TBDPS protecting groups as efficient aryl group donors in Pd-catalyzed arylation of phenols and anilines.

Authors:  Chunhui Huang; Vladimir Gevorgyan
Journal:  J Am Chem Soc       Date:  2009-08-12       Impact factor: 15.419
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  2 in total

1.  Palladium-catalyzed carbonylative cyclization/arylation cascade for 2-aroylindolizine synthesis.

Authors:  Zhou Li; Dmitri Chernyak; Vladimir Gevorgyan
Journal:  Org Lett       Date:  2012-11-28       Impact factor: 6.005

2.  Cu-Catalyzed Transannulation Reaction of Pyridotriazoles with Terminal Alkynes under Aerobic Conditions: Efficient Synthesis of Indolizines.

Authors:  V Helan; A V Gulevich; V Gevorgyan
Journal:  Chem Sci       Date:  2015-03       Impact factor: 9.825
  2 in total

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