Literature DB >> 16895427

Intramolecular diels-alder/1,3-dipolar cycloaddition cascade of 1,3,4-oxadiazoles.

Gregory I Elliott1, James R Fuchs, Brian S J Blagg, Hayato Ishikawa, Houchao Tao, Z-Q Yuan, Dale L Boger.   

Abstract

Full details of a systematic exploration of the intramolecular [4 + 2]/[3 + 2] cycloaddition cascade of 1,3,4-oxadiazoles are disclosed in which the scope and utility of the reaction are defined.

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Year:  2006        PMID： 16895427      PMCID： PMC2587417          DOI： 10.1021/ja0612549

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  8 in total

1.  Total synthesis of anhydrolycorinone utilizing sequential intramolecular Diels-Alder reactions of a 1,3,4-oxadiazole.

Authors:  Scott E Wolkenberg; Dale L Boger
Journal:  J Org Chem       Date:  2002-10-18       Impact factor: 4.354

2.  Intramolecular Diels-Alder and tandem intramolecular Diels-Alder/1,3-dipolar cycloaddition reactions of 1,3,4-oxadiazoles.

Authors:  Gordon D Wilkie; Gregory I Elliott; Brian S J Blagg; Scott E Wolkenberg; Danielle R Soenen; Michael M Miller; Scott Pollack; Dale L Boger
Journal:  J Am Chem Soc       Date:  2002-09-25       Impact factor: 15.419

3.  Intramolecular [3 + 2]-cycloaddition reaction of push-pull dipoles across heteroaromatic pi-systems.

Authors:  José M Mejía-Oneto; Albert Padwa
Journal:  Org Lett       Date:  2004-09-16       Impact factor: 6.005

4.  Total synthesis of (-)- and ent-(+)-vindoline.

Authors:  Younggi Choi; Hayato Ishikawa; Juraj Velcicky; Gregory I Elliott; Michael M Miller; Dale L Boger
Journal:  Org Lett       Date:  2005-09-29       Impact factor: 6.005

5.  Total synthesis of (-)- and ent-(+)-vindorosine: tandem intramolecular Diels-Alder/1,3-dipolar cycloaddition of 1,3,4-oxadiazoles.

Authors:  Gregory I Elliott; Juraj Velcicky; Hayato Ishikawa; Yongkai Li; Dale L Boger
Journal:  Angew Chem Int Ed Engl       Date:  2006-01-16       Impact factor: 15.336

6.  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

7.  Synthesis of the Pentacyclic Skeleton of the Aspidosperma Alkaloids Using Rhodium Carbenoids as Reactive Intermediates.

Authors:  Albert Padwa; Alan T. Price
Journal:  J Org Chem       Date:  1998-02-06       Impact factor: 4.354

8.  Total synthesis of natural (+)- [corrected] and ent-(-)-4-desacetoxy-6,7-dihydrovindorosine [corrected] and natural and ent-minovine: oxadiazole tandem intramolecular Diels-Alder/1,3-dipolar cycloaddition reaction.

Authors:  Zhong Qing Yuan; Hayato Ishikawa; Dale L Boger
Journal:  Org Lett       Date:  2005-02-17       Impact factor: 6.005
  8 in total
  41 in total

1.  Synthesis and Biological Evaluation of Bile Acid Analogues Inhibitory to Clostridium difficile Spore Germination.

Authors:  Kristen L Stoltz; Raymond Erickson; Christopher Staley; Alexa R Weingarden; Erin Romens; Clifford J Steer; Alexander Khoruts; Michael J Sadowsky; Peter I Dosa
Journal:  J Med Chem       Date:  2017-04-12       Impact factor: 7.446

2.  Synthesis, Characterization, and Rapid Cycloadditions of 5-Nitro-1,2,3-triazine.

Authors:  Christopher M Glinkerman; Dale L Boger
Journal:  Org Lett       Date:  2018-04-16       Impact factor: 6.005

3.  Cycloadditions of 1,2,3-Triazines Bearing C5-Electron Donating Substituents: Robust Pyrimidine Synthesis.

Authors:  Christopher M Glinkerman; Dale L Boger
Journal:  Org Lett       Date:  2015-07-14       Impact factor: 6.005

4.  Inverse electron demand Diels-Alder reactions of 1,2,3-triazines: pronounced substituent effects on reactivity and cycloaddition scope.

Authors:  Erin D Anderson; Dale L Boger
Journal:  J Am Chem Soc       Date:  2011-07-19       Impact factor: 15.419

5.  Total synthesis of (-)- and ent-(+)-vindoline and related alkaloids.

Authors:  Hayato Ishikawa; Gregory I Elliott; Juraj Velcicky; Younggi Choi; Dale L Boger
Journal:  J Am Chem Soc       Date:  2006-08-16       Impact factor: 15.419

6.  Total synthesis of vinblastine, vincristine, related natural products, and key structural analogues.

Authors:  Hayato Ishikawa; David A Colby; Shigeki Seto; Porino Va; Annie Tam; Hiroyuki Kakei; Thomas J Rayl; Inkyu Hwang; Dale L Boger
Journal:  J Am Chem Soc       Date:  2009-04-08       Impact factor: 15.419

7.  Total synthesis and evaluation of vinblastine analogues containing systematic deep-seated modifications in the vindoline subunit ring system: core redesign.

Authors:  Kristin D Schleicher; Yoshikazu Sasaki; Annie Tam; Daisuke Kato; Katharine K Duncan; Dale L Boger
Journal:  J Med Chem       Date:  2013-01-04       Impact factor: 7.446

8.  A remarkable series of vinblastine analogues displaying enhanced activity and an unprecedented tubulin binding steric tolerance: C20' urea derivatives.

Authors:  Erick K Leggans; Katharine K Duncan; Timothy J Barker; Kristin D Schleicher; Dale L Boger
Journal:  J Med Chem       Date:  2012-12-17       Impact factor: 7.446

9.  Divergent Total Syntheses of (-)-Pseudocopsinine and (-)-Minovincinine.

Authors:  Xianhuang Zeng; Vyom Shukla; Dale L Boger
Journal:  J Org Chem       Date:  2020-11-18       Impact factor: 4.354

10.  Vinblastine 20' Amides: Synthetic Analogues That Maintain or Improve Potency and Simultaneously Overcome Pgp-Derived Efflux and Resistance.

Authors:  John C Lukesh; Daniel W Carney; Huijun Dong; R Matthew Cross; Vyom Shukla; Katharine K Duncan; Shouliang Yang; Daniel M Brody; Manuela M Brütsch; Aleksandar Radakovic; Dale L Boger
Journal:  J Med Chem       Date:  2017-08-31       Impact factor: 7.446
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