Literature DB >> 14507203

Synthesis of novel tetracycles via an intramolecular Heck reaction with anti-hydride elimination.

Mark Lautens1, Yuan-Qing Fang.   

Abstract

[reaction: see text] The catalytic combination of Pd(2)(dba)(3)/HP(t-Bu)(3).BF(4) and DABCO gives an unusual intramolecular Heck reaction with dihydronaphthalene substrates, yielding formal anti-hydride elimination products in good to excellent yields under mild conditions. For dibromo substrates, multiple Heck reactions are possible when an external acceptor is added to afford more highly functionalized products.

Entities:  

Year:  2003        PMID: 14507203     DOI: 10.1021/ol035354k

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


  9 in total

Review 1.  Direct transition metal-catalyzed functionalization of heteroaromatic compounds.

Authors:  Ilya V Seregin; Vladimir Gevorgyan
Journal:  Chem Soc Rev       Date:  2007-03-05       Impact factor: 54.564

2.  Palladium-catalyzed direct functionalization of imidazolinone: synthesis of dibromophakellstatin.

Authors:  Jianming Lu; Xianghui Tan; Chuo Chen
Journal:  J Am Chem Soc       Date:  2007-06-01       Impact factor: 15.419

Review 3.  Chemistry, biology, and medicinal potential of narciclasine and its congeners.

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Journal:  Chem Rev       Date:  2008-05-20       Impact factor: 60.622

4.  Oxidative cyclizations in a nonpolar solvent using molecular oxygen and studies on the stereochemistry of oxypalladation.

Authors:  Raissa M Trend; Yeeman K Ramtohul; Brian M Stoltz
Journal:  J Am Chem Soc       Date:  2005-12-21       Impact factor: 15.419

5.  Total Synthesis of (-)-Nodulisporic Acid D.

Authors:  Yike Zou; Jason E Melvin; Stephen S Gonzales; Matthew J Spafford; Amos B Smith
Journal:  J Am Chem Soc       Date:  2015-06-01       Impact factor: 15.419

6.  Palladium-catalyzed method for the synthesis of carbazoles via tandem C-H functionalization and C-N bond formation.

Authors:  W C Peter Tsang; Rachel H Munday; Gordon Brasche; Nan Zheng; Stephen L Buchwald
Journal:  J Org Chem       Date:  2008-08-29       Impact factor: 4.354

7.  Synthesis and biological evaluation of 10-benzyloxy-Narciclasine.

Authors:  Vincenzo Ticli; Zhenze Zhao; Liqin Du; Alexander Kornienko; Tomas Hudlicky
Journal:  Tetrahedron       Date:  2021-10-18       Impact factor: 2.457

8.  Well-Defined and Robust Rhodium Catalysts for the Hydroacylation of Terminal and Internal Alkenes.

Authors:  Amparo Prades; Maitane Fernández; Sebastian D Pike; Michael C Willis; Andrew S Weller
Journal:  Angew Chem Int Ed Engl       Date:  2015-06-09       Impact factor: 15.336

9.  Total synthesis of (+)-linoxepin by utilizing the Catellani reaction.

Authors:  Harald Weinstabl; Marcel Suhartono; Zafar Qureshi; Mark Lautens
Journal:  Angew Chem Int Ed Engl       Date:  2013-04-16       Impact factor: 15.336

  9 in total

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