Literature DB >> 16805559

A [3 + 3] annelation approach to tetrahydropyridines.

Lisa C Pattenden1, Robert A J Wybrow, Stephen A Smith, Joseph P A Harrity.   

Abstract

[reaction: see text] A stepwise [3+3] annelation sequence to tetrahydropyridines via addition of the Büchi Grignard to aziridines has been developed. These intermediates can be further functionalized with good regio- and stereocontrol and this methodology has been employed in the stereoselective formal synthesis of (-)-dihydropinidine.

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Year:  2006        PMID： 16805559     DOI： 10.1021/ol0610789

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  10 in total

1.  Highly stereoselective formal [3 + 3] cycloaddition of enals and azomethine imines catalyzed by N-heterocyclic carbenes.

Authors:  Audrey Chan; Karl A Scheidt
Journal:  J Am Chem Soc       Date:  2007-04-04       Impact factor: 15.419

2.  Identification of a 2-phenyl-substituted octahydrobenzo[f]quinoline as a dopamine D₃ receptor-selective full agonist ligand.

Authors:  Alia H Clark; John D McCorvy; Jason M Conley; Whitney K Williams; Markondaiah Bekkam; Val J Watts; David E Nichols
Journal:  Bioorg Med Chem       Date:  2012-09-08       Impact factor: 3.641

3.  Aza-[3 + 3] Annulations: A New Unified Strategy in Alkaloid Synthesis.

Authors:  Grant S Buchanan; John B Feltenberger; Richard P Hsung
Journal:  Curr Org Synth       Date:  2010-08-01       Impact factor: 1.975

4.  A Stereodivergent Approach for Accessing Both C2,8a-Syn and C2,8a-Anti Relative Stereochemical Manifolds in the Lepadin Family via a TiCL(4)-Promoted Aza-[3 + 3] Annulation.

Authors:  Gang Li; Lauren J Carlson; Irina K Sagamanova; Brian W Slafer; Richard P Hsung; Claudio Gilardi; Heather M Sklenicka; Nadiya Sydroenko
Journal:  Synthesis (Stuttg)       Date:  2009-09-01       Impact factor: 3.157

5.  Aza- and Carbo-[3 + 3] Annulations of Exo-Cyclic Vinylogous Amides and Urethanes. Synthesis of Tetrahydroindolizidines and An Unexpected Formation of Hexahydroquinolines.

Authors:  Sunil K Ghosh; Grant S Buchanan; Quincy A Long; Yonggang Wei; Ziyad F Al-Rashid; Heather M Sklenicka; Richard P Hsung
Journal:  Tetrahedron       Date:  2008-01-28       Impact factor: 2.457

6.  Total synthesis of (+)-lepadin F.

Authors:  Gang Li; Richard P Hsung; Brian W Slafer; Irina K Sagamanova
Journal:  Org Lett       Date:  2008-09-27       Impact factor: 6.005

7.  A General Approach to the Quinolizidine Alkaloids via an Intramolecular Aza-[3 + 3] Annulation. Synthesis of (±)-2-Deoxy-Lasubine II.

Authors:  Yu Zhang; Aleksey I Gerasyuto; Quincy A Long; Richard P Hsung
Journal:  Synlett       Date:  2008-01-01       Impact factor: 2.454

8.  The [3 + 3]-cycloaddition alternative for heterocycle syntheses: catalytically generated metalloenolcarbenes as dipolar adducts.

Authors:  Xinfang Xu; Michael P Doyle
Journal:  Acc Chem Res       Date:  2014-03-20       Impact factor: 22.384

9.  Phosphine-Promoted [4 + 3] Annulation of Allenoate with Aziridines for Synthesis of Tetrahydroazepines: Phosphine-Dependent [3 + 3] and [4 + 3] Pathways.

Authors:  Honglei Liu; Yan Lin; Yan Zhao; Miaoren Xiao; Leijie Zhou; Qijun Wang; Cheng Zhang; Dongqi Wang; Ohyun Kwon; Hongchao Guo
Journal:  RSC Adv       Date:  2019-01-09       Impact factor: 4.036

10.  Pd-catalysed [3 + 3] annelations in the stereoselective synthesis of indolizidines.

Authors:  Olivier Y Provoost; Andrew J Hazelwood; Joseph P A Harrity
Journal:  Beilstein J Org Chem       Date:  2007-02-08       Impact factor: 2.883
  10 in total

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