Jump to main content
Jump to site search

Issue 85, 2016
Previous Article Next Article

2-Nitropyrrole cross-coupling enables a second generation synthesis of the heronapyrrole antibiotic natural product family

Author affiliations

Abstract

The heronapyrroles are a family of antibiotic natural products containing the rare 2-nitropyrrole motif. We report here a second generation total synthesis that circumvents problems of selective pyrrole nitration and alkene formation that limited the utility of previous approaches. Stille sp3–sp2 cross coupling of a novel 2-nitropyrrole fragment was developed to install the key C7,8 olefin with complete regiochemical control. An unusual Hunsdiecker-type decarboxylative halogenation was also identified, providing access to the complex vinyl stannane coupling partners required for formation of the natural product.

Graphical abstract: 2-Nitropyrrole cross-coupling enables a second generation synthesis of the heronapyrrole antibiotic natural product family

Back to tab navigation

Supplementary files

Publication details

The article was received on 15 Sep 2016, accepted on 29 Sep 2016 and first published on 30 Sep 2016


Article type: Communication
DOI: 10.1039/C6CC07532K
Citation: Chem. Commun., 2016,52, 12638-12641
  •   Request permissions

    2-Nitropyrrole cross-coupling enables a second generation synthesis of the heronapyrrole antibiotic natural product family

    X. Ding, D. P. Furkert and M. A. Brimble, Chem. Commun., 2016, 52, 12638
    DOI: 10.1039/C6CC07532K

Search articles by author

Spotlight

Advertisements