Literature DB >> 11149859

Total synthesis of Amaryllidaceae alkaloids utilizing sequential intramolecular heterocyclic azadiene Diels-Alder reactions of an unsymmetrical 1,2,4,5-tetrazine.

D L Boger1, S E Wolkenberg.   

Abstract

Convergent total syntheses of anhydrolycorinone, hippadine, and anhydrolycorinium chloride are detailed, enlisting sequential inverse electron demand Diels-Alder reactions of an unsymmetrical N-acyl-6-amino-1,2,4,5-tetrazine.

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Year:  2000        PMID： 11149859     DOI： 10.1021/jo0012546

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  12 in total

1.  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

2.  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

3.  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

4.  Scope of the inverse electron demand Diels-Alder reactions of 1,2,3-triazine.

Authors:  Erin D Anderson; Dale L Boger
Journal:  Org Lett       Date:  2011-04-13       Impact factor: 6.005

5.  Total synthesis of lycogarubin C and lycogalic acid.

Authors:  James S Oakdale; Dale L Boger
Journal:  Org Lett       Date:  2010-03-05       Impact factor: 6.005

6.  Direct Synthesis of β-Aminoenals through Reaction of 1,2,3-Triazine with Secondary Amines.

Authors:  Ryan E Quiñones; Christopher M Glinkerman; Kaicheng Zhu; Dale L Boger
Journal:  Org Lett       Date:  2017-06-28       Impact factor: 6.005

7.  Approach toward the total synthesis of 5-hydroxyaloin A.

Authors:  Kristen J Procko; Hui Li; Stephen F Martin
Journal:  Org Lett       Date:  2010-11-17       Impact factor: 6.005

8.  Two novel 1,2,4,5-tetrazines that participate in inverse electron demand Diels-Alder reactions with an unexpected regioselectivity.

Authors:  Akiyuki Hamasaki; Richard Ducray; Dale L Boger
Journal:  J Org Chem       Date:  2006-01-06       Impact factor: 4.354

Review 9.  Inverse Electron Demand Diels-Alder Reactions of Heterocyclic Azadienes, 1-Aza-1,3-Butadienes, Cyclopropenone Ketals, and Related Systems. A Retrospective.

Authors:  Jiajun Zhang; Vyom Shukla; Dale L Boger
Journal:  J Org Chem       Date:  2019-05-23       Impact factor: 4.354

10.  Toward phenanthridin-2-ylidene: electrophilicity versus acidity in planar-constrained C-aryl iminium salts.

Authors:  Xavier Cattoën; Didier Bourissou; Guy Bertrand
Journal:  Tetrahedron Lett       Date:  2006       Impact factor: 2.415
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