Literature DB >> 12785818

Total synthesis of the salicylate enamide macrolide oximidine II.

Xiang Wang1, John A Porco.   

Abstract

The asymmetric synthesis of the salicylate enamide macrolide oximidine II is reported. The synthesis involves a highly regio- and stereoselective ring-closing metathesis of a bis-diene substrate to construct the macrocyclic triene core. Copper(I)-mediated amidation of a (Z)-vinyl iodide was employed to attach the enamide side chain.

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Year:  2003        PMID: 12785818     DOI: 10.1021/ja034030o

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


  5 in total

1.  Diamine Ligands in Copper-Catalyzed Reactions.

Authors:  David S Surry; Stephen L Buchwald
Journal:  Chem Sci       Date:  2010       Impact factor: 9.825

2.  Synthesis of oximidine II by a copper-mediated reductive ene-yne macrocyclization.

Authors:  Christopher M Schneider; Kriangsak Khownium; Wei Li; Jared T Spletstoser; Torsten Haack; Gunda I Georg
Journal:  Angew Chem Int Ed Engl       Date:  2011-06-29       Impact factor: 15.336

3.  Development of a general, sequential, ring-closing metathesis/intramolecular cross-coupling reaction for the synthesis of polyunsaturated macrolactones.

Authors:  Scott E Denmark; Joseck M Muhuhi
Journal:  J Am Chem Soc       Date:  2010-08-25       Impact factor: 15.419

4.  Formation of macrocyclic lactones in the Paternò-Büchi dimerization reaction.

Authors:  Junya Arimura; Tsutomu Mizuta; Yoshikazu Hiraga; Manabu Abe
Journal:  Beilstein J Org Chem       Date:  2011-02-28       Impact factor: 2.883

5.  Enantiospecific Synthesis and Cytotoxicity Evaluation of Oximidine II Analogues.

Authors:  Christopher M Schneider; Wei Li; Kriangsak Khownium; Gerald H Lushington; Gunda I Georg
Journal:  ChemMedChem       Date:  2016-05-31       Impact factor: 3.466

  5 in total

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