Literature DB >> 10986080

Synthesis of 2-fluoro-6-O-propargyl-11,12-carbamate ketolides. A novel class of antibiotics.

L T Phan1, R F Clark, M Rupp, Y S Or, D T Chu, Z Ma.   

Abstract

A novel class of 2-fluoro-6-O-propargyl-11,12-carbamate ketolide derivatives of erythromycin has been synthesized for antibacterial SAR studies. Replacement of the C2-hydrogen by a fluorine atom allows the synthesis of 6-O-propargylic ketones and electron-deficient 6-O-propargylic aromatic derivatives by preventing intramolecular C2-enolate Michael cyclization.

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Year:  2000        PMID: 10986080     DOI: 10.1021/ol006226o

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


  5 in total

1.  Semisynthetic preparation of leucomycin derivatives: introduction of aromatic side chains by reductive amination.

Authors:  Peter Gebhardt; Udo Gräfe; Ute Möllmann; Christian Hertweck
Journal:  Mol Divers       Date:  2005       Impact factor: 2.943

Review 2.  The ketolides: a critical review.

Authors:  George G Zhanel; Michael Walters; Ayman Noreddin; Lavern M Vercaigne; Aleksandra Wierzbowski; John M Embil; Alfred S Gin; Stephen Douthwaite; Daryl J Hoban
Journal:  Drugs       Date:  2002       Impact factor: 9.546

3.  Recyclable fluorous cinchona alkaloid ester as a chiral promoter for asymmetric fluorination of β-ketoesters.

Authors:  Wen-Bin Yi; Xin Huang; Zijuan Zhang; Dian-Rong Zhu; Chun Cai; Wei Zhang
Journal:  Beilstein J Org Chem       Date:  2012-08-03       Impact factor: 2.883

4.  Development of the titanium-TADDOLate-catalyzed asymmetric fluorination of β-ketoesters.

Authors:  Lukas Hintermann; Mauro Perseghini; Antonio Togni
Journal:  Beilstein J Org Chem       Date:  2011-10-17       Impact factor: 2.883

Review 5.  Scaffold Modifications in Erythromycin Macrolide Antibiotics. A Chemical Minireview.

Authors:  Kjell Undheim
Journal:  Molecules       Date:  2020-08-28       Impact factor: 4.411

  5 in total

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