Literature DB >> 18154343

A metathesis-based approach to the synthesis of 2-pyridones and pyridines.

Timothy J Donohoe1, Lisa P Fishlock, Panayiotis A Procopiou.   

Abstract

The ring-closing metathesis reaction has been successfully employed to form a range of dihydropyridone intermediates, which are in the correct oxidation state to undergo a base-induced elimination to reveal the aromatic 2-pyridone. This mild and novel approach to six-membered heteroaromatic compounds then provides access to a wide variety of substituted pyridines in excellent overall yield.

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Year:  2007        PMID： 18154343     DOI： 10.1021/ol702684d

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


  8 in total

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2.  Olefin cross-metathesis-based approaches to furans: procedures for the preparation of di- and trisubstituted variants.

Authors:  Timothy J Donohoe; John F Bower; José A Basutto
Journal:  Nat Protoc       Date:  2010-12-02       Impact factor: 13.491

3.  An expedient route to substituted furans via olefin cross-metathesis.

Authors:  Timothy J Donohoe; John F Bower
Journal:  Proc Natl Acad Sci U S A       Date:  2010-02-08       Impact factor: 11.205

4.  A mild and efficient approach to enantioenriched α-hydroxyethyl α,β-unsaturated δ-lactams.

Authors:  Seo-Jung Han; Brian M Stoltz
Journal:  Tetrahedron Lett       Date:  2016-05-25       Impact factor: 2.415

5.  The lyconadins: enantioselective total syntheses of (+)-lyconadin A and (-)-lyconadin B.

Authors:  Douglas C Beshore; Amos B Smith
Journal:  J Am Chem Soc       Date:  2008-09-18       Impact factor: 15.419

6.  Exploration of an epoxidation-ring-opening strategy for the synthesis of lyconadin A and discovery of an unexpected Payne rearrangement.

Authors:  Brad M Loertscher; Yu Zhang; Steven L Castle
Journal:  Beilstein J Org Chem       Date:  2013-06-18       Impact factor: 2.883

7.  Total synthesis of the antitumor antibiotic (±)-streptonigrin: first- and second-generation routes for de novo pyridine formation using ring-closing metathesis.

Authors:  Timothy J Donohoe; Christopher R Jones; Anne F Kornahrens; Luiz C A Barbosa; Louise J Walport; Matthew R Tatton; Michael O'Hagan; Akshat H Rathi; David B Baker
Journal:  J Org Chem       Date:  2013-12-12       Impact factor: 4.354

8.  Isothiourea-mediated one-pot synthesis of functionalized pyridines.

Authors:  Daniel G Stark; Louis C Morrill; Pei-Pei Yeh; Alexandra M Z Slawin; Timothy J C O'Riordan; Andrew D Smith
Journal:  Angew Chem Int Ed Engl       Date:  2013-09-17       Impact factor: 15.336
  8 in total

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