Literature DB >> 26456984

Synthesis of Substituted Tropones by Sequential Rh-Catalyzed [5+2] Cycloaddition and Elimination.

Wangze Song1, Bao-Min Xi2, Ka Yang1, Weiping Tang3.   

Abstract

Highly substituted tropones are prepared from cycloheptatrienes derived from Rh-catalyzed intermolecular [5+2] cycloaddition of 3-acyloxy-1,4-enynes and propargylic alcohols. The intermolecular [5+2] cycloaddition is highly regioselective for a variety of propargylic alcohols. Elimination of the cycloaddition products afforded various substituted tropones.

Entities:  

Keywords:  1,4-enynes; alkynes; cycloaddition; rhodium; tropone

Year:  2015        PMID： 26456984      PMCID： PMC4597182          DOI： 10.1016/j.tet.2015.04.039

Source DB:  PubMed          Journal:  Tetrahedron        ISSN： 0040-4020            Impact factor:   2.457


  24 in total

1.  The cycloaddition strategy for the synthesis of natural products containing carbocyclic seven-membered rings.

Authors:  Merle A Battiste; Phillip M Pelphrey; Dennis L Wright
Journal:  Chemistry       Date:  2006-04-24       Impact factor: 5.236

Review 2.  A fresh look at natural tropolonoids.

Authors:  Ronald Bentley
Journal:  Nat Prod Rep       Date:  2007-11-22       Impact factor: 13.423

3.  Triflic acid-mediated rearrangements of 3-methoxy-8-oxabicyclo[3.2.1]octa-3,6-dien-2-ones: synthesis of methoxytropolones and furans.

Authors:  Yvonne D Williams; Christine Meck; Noushad Mohd; Ryan P Murelli
Journal:  J Org Chem       Date:  2013-11-14       Impact factor: 4.354

4.  Cu(I)-catalyzed regio- and stereoselective [6 + 3] cycloaddition of azomethine ylides with tropone: an efficient asymmetric access to bridged azabicyclo[4.3.1]decadienes.

Authors:  Huai-Long Teng; Lu Yao; Chun-Jiang Wang
Journal:  J Am Chem Soc       Date:  2014-03-04       Impact factor: 15.419

5.  Interception of a Rautenstrauch intermediate by alkynes for [5+2] cycloaddition: rhodium-catalyzed cycloisomerization of 3-acyloxy-4-ene-1,9-diynes to bicyclo[5.3.0]decatrienes.

Authors:  Xing-zhong Shu; Suyu Huang; Dongxu Shu; Ilia A Guzei; Weiping Tang
Journal:  Angew Chem Int Ed Engl       Date:  2011-07-11       Impact factor: 15.336

6.  Tropolones as lead-like natural products: the development of potent and selective histone deacetylase inhibitors.

Authors:  Sophia N Ononye; Michael D VanHeyst; E Zachary Oblak; Wangda Zhou; Mohamed Ammar; Amy C Anderson; Dennis L Wright
Journal:  ACS Med Chem Lett       Date:  2013-06-10       Impact factor: 4.345

7.  Transfer of chirality in the rhodium-catalyzed intramolecular [5+2] cycloaddition of 3-acyloxy-1,4-enynes (ACEs) and alkynes: synthesis of enantioenriched bicyclo[5.3.0]decatrienes.

Authors:  Xing-Zhong Shu; Casi M Schienebeck; Wangze Song; Ilia A Guzei; Weiping Tang
Journal:  Angew Chem Int Ed Engl       Date:  2013-10-21       Impact factor: 15.336

8.  An N-heterocyclic carbene-catalyzed [8 + 3] annulation of tropone and enals via homoenolate.

Authors:  Vijay Nair; Manojkumar Poonoth; Sreekumar Vellalath; Eringathodi Suresh; Rajasekaran Thirumalai
Journal:  J Org Chem       Date:  2006-11-10       Impact factor: 4.354

9.  Asymmetric synthesis of bicyclo[4.3.1]decadienes and bicyclo[3.3.2]decadienes via [6 + 3] trimethylenemethane cycloaddition with tropones.

Authors:  Barry M Trost; Patrick J McDougall; Olaf Hartmann; Peter T Wathen
Journal:  J Am Chem Soc       Date:  2008-10-21       Impact factor: 15.419

10.  Inhibition of the ANT(2")-Ia resistance enzyme and rescue of aminoglycoside antibiotic activity by synthetic α-hydroxytropolones.

Authors:  Danielle R Hirsch; Georgina Cox; Michael P D'Erasmo; Tushar Shakya; Christine Meck; Noushad Mohd; Gerard D Wright; Ryan P Murelli
Journal:  Bioorg Med Chem Lett       Date:  2014-09-19       Impact factor: 2.823
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  1 in total

Review 1.  Rhodium-Catalyzed (5 + 2) and (5 + 1) Cycloadditions Using 1,4-Enynes as Five-Carbon Building Blocks.

Authors:  Stephanie A Blaszczyk; Daniel A Glazier; Weiping Tang
Journal:  Acc Chem Res       Date:  2019-12-10       Impact factor: 22.384
  1 in total

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