Literature DB >> 21857757

Intramolecular Cyclization Strategies Toward the Synthesis of Zoanthamine Alkaloids.

Derek Fischer1, Thong X Nguyen, Lynnie Trzoss, Marianna Dakanali, Emmanuel A Theodorakis.   

Abstract

Stabilized 2-amino-1,3-dienes can participate in intramolecular Diels-Alder (IMDA) reactions with pendant dienophiles. We found that these dienes can be readily prepared via standard palladium-mediated coupling reactions and have comparable reactivity to 2-oxodienes. Application of these substrates to the synthesis of tetracyclic model systems representing the ABCE motif of the zoanthamines is presented.

Entities:  

Year:  2011        PMID： 21857757      PMCID： PMC3157960          DOI： 10.1016/j.tetlet.2011.07.054

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


  27 in total

1.  Experimental and computational studies into an ATPH-promoted exo-selective IMDA reaction: a short total synthesis of Delta9-THC.

Authors:  Emma L Pearson; Nicholas Kanizaj; Anthony C Willis; Michael N Paddon-Row; Michael S Sherburn
Journal:  Chemistry       Date:  2010-07-26       Impact factor: 5.236

2.  Stereocontrolled formation of epoxy peroxide functionality appended to a lactam ring.

Authors:  C M Marson; A Khan; R A Porter
Journal:  J Org Chem       Date:  2001-07-13       Impact factor: 4.354

Review 3.  The biology and chemistry of the zoanthamine alkaloids.

Authors:  Douglas C Behenna; Jennifer L Stockdill; Brian M Stoltz
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

4.  Total synthesis and absolute stereochemical assignment of (+)- and (-)-galbulimima alkaloid 13.

Authors:  Mohammad Movassaghi; Diana K Hunt; Meiliana Tjandra
Journal:  J Am Chem Soc       Date:  2006-06-28       Impact factor: 15.419

5.  A concise and convergent route to 5,8-disubstituted indolizidine and 1,4-disubstituted quinolizidine ring cores by diastereoselective aza-Diels-Alder reaction.

Authors:  José Barluenga; Carlos Mateos; Fernando Aznar; Carlos Valdés
Journal:  Org Lett       Date:  2002-05-30       Impact factor: 6.005

6.  New approach to 2-quinolinones.

Authors:  Cheng-Chieh Huang; Nein-Chen Chang
Journal:  Org Lett       Date:  2008-01-19       Impact factor: 6.005

7.  Preparation and cycloaddition reactions of enantiopure 2-(N-acylamino)-1,3-dienes for the synthesis of octahydroquinoline derivatives.

Authors:  Fabrizio Lo Galbo; Ernesto G Occhiato; Antonio Guarna; Cristina Faggi
Journal:  J Org Chem       Date:  2003-08-08       Impact factor: 4.354

8.  Controlling cis/trans-selectivity in intramolecular Diels-Alder reactions of benzo-tethered, ester linked 1,3,9-decatrienes.

Authors:  Emma L Pearson; Anthony C Willis; Michael S Sherburn; Michael N Paddon-Row
Journal:  Org Biomol Chem       Date:  2007-12-13       Impact factor: 3.876

9.  Air stable, sterically hindered ferrocenyl dialkylphosphines for palladium-catalyzed C[bond]C, C[bond]N, and C[bond]O bond-forming cross-couplings.

Authors:  Noriyasu Kataoka; Quinetta Shelby; James P Stambuli; John F Hartwig
Journal:  J Org Chem       Date:  2002-08-09       Impact factor: 4.354

10.  Total synthesis of (-)-himandrine.

Authors:  Mohammad Movassaghi; Meiliana Tjandra; Jun Qi
Journal:  J Am Chem Soc       Date:  2009-07-22       Impact factor: 15.419
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  2 in total

1.  Synthetic Strategies Toward the Decalin Motif of Maklamicin and Related Spirotetronates.

Authors:  Michelle H Lacoske; Jing Xu; Noel Mansour; Chao Gao; Emmanuel A Theodorakis
Journal:  Org Chem Front       Date:  2015-04-01       Impact factor: 5.281

2.  Zoanthamine Alkaloids from the Zoantharian Zoanthus cf. pulchellus and Their Effects in Neuroinflammation.

Authors:  Paul O Guillen; Sandra Gegunde; Karla B Jaramillo; Amparo Alfonso; Kevin Calabro; Eva Alonso; Jenny Rodriguez; Luis M Botana; Olivier P Thomas
Journal:  Mar Drugs       Date:  2018-07-20       Impact factor: 5.118
  2 in total

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