Literature DB >> 20548964

Synthesis of hydronaphthalenes through coupling of enyne carbonyl compounds that contain pendant alkene groups with Fischer carbene complexes.

Rajesh Kumar-Patti1, Shaofeng Duan, Alejandro Camacho-Davila, Kris Waynant, Kenneth A Dunn, James W Herndon.   

Abstract

The coupling of enyne carbonyl compounds that contain pendant alkene groups with Fischer carbene complexes to afford furans that contain pendant alkene groups is described. Subsequent intramolecular Diels-Alder reactions are effective in select cases, resulting in hydronaphthalene systems after dehydration. Although the Diels-Alder event is thermodynamically unfavorable, the overall transformation of alkene-furans to dihydronaphthalenes is a favorable process.

Entities:  

Year:  2010        PMID： 20548964      PMCID： PMC2883779          DOI： 10.1016/j.tetlet.2010.05.049

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  7 in total

1.  Studies on the synthesis of (+/-)-stenine: a combined intramolecular [4 + 2]-cycloaddition/rearrangement cascade.

Authors:  Albert Padwa; John D Ginn
Journal:  J Org Chem       Date:  2005-06-24       Impact factor: 4.354

2.  Synthesis of azapolycyclic systems via the intramolecular [4 + 2] cycloaddition chemistry of 2-(alkylthio)-5-amidofurans.

Authors:  Albert Padwa; John D Ginn; Scott K Bur; Cheryl K Eidell; Stephen M Lynch
Journal:  J Org Chem       Date:  2002-05-17       Impact factor: 4.354

3.  A stereoselective and atom-efficient approach to multifunctionalized five- and six-membered rings via a novel michael-initiated intramolecular Diels-Alder furan reaction.

Authors:  Irishi N N Namboothiri; Madhu Ganesh; Shaikh M Mobin; Miriam Cojocaru
Journal:  J Org Chem       Date:  2005-03-18       Impact factor: 4.354

4.  Cycloaddition chemistry of 2-vinyl-substituted indoles and related heteroaromatic systems.

Authors:  Albert Padwa; Stephen M Lynch; José M Mejía-Oneto; Hongjun Zhang
Journal:  J Org Chem       Date:  2005-03-18       Impact factor: 4.354

5.  Intramolecular Diels-Alder reactions of optically active allenic ketones: chirality transfer in the preparation of substituted oxa-bridged octalones.

Authors:  Michael E Jung; Sun-Joon Min
Journal:  J Am Chem Soc       Date:  2005-08-10       Impact factor: 15.419

6.  Synthesis of phenanthrene derivatives through the net [5+5]-cycloaddition of prenylated carbene complexes with 2-alkynylbenzaldehyde derivatives.

Authors:  Suneetha Menon; Dilip Sinha-Mahapatra; James W Herndon
Journal:  Tetrahedron       Date:  2007-09-03       Impact factor: 2.457

7.  Rh(I)-catalyzed ring opening of an IMDAF-derived oxabicyclo cycloadduct as the key step in the synthesis of (+/-)-epi-zephyranthine.

Authors:  Qiu Wang; Albert Padwa
Journal:  Org Lett       Date:  2004-06-24       Impact factor: 6.005
  7 in total
  1 in total

1.  The [5+5] route to the phenanthrene skeleton.

Authors:  James W Herndon; Bishnu Dhakal
Journal:  ARKIVOC       Date:  2016-06-21       Impact factor: 1.140
  1 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.