title: 2-Nitropyrrole cross-coupling enables a second generation synthesis of the heronapyrrole antibiotic natural product family.
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-sp2cross 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.
authors.affiliation: School of Chemical Sciences, University of Auckland, 23 Symonds St., Auckland 1010, New Zealand. m.brimble@auckland.ac.nz.
authors.forename: Xiao-Bo
authors.initials: XB
authors.lastname: Ding
authors.affiliation: School of Chemical Sciences, University of Auckland, 23 Symonds St., Auckland 1010, New Zealand. m.brimble@auckland.ac.nz.
authors.forename: Daniel P
authors.identifier: http://orcid.org/0000-0001-6286-9105
authors.initials: DP
authors.lastname: Furkert
authors.affiliation: School of Chemical Sciences, University of Auckland, 23 Symonds St., Auckland 1010, New Zealand. m.brimble@auckland.ac.nz and Maurice Wilkins Centre for Molecular Biodiscovery, University of Auckland, Private Bag 92019, Auckland 1010, New Zealand.
authors.forename: Margaret A
authors.identifier: http://orcid.org/0000-0002-7086-4096
authors.initials: MA
authors.lastname: Brimble
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis*; D001688:Biological Products / Q000138:chemical synthesis*; D015394:Molecular Structure; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism; D013302:Streptomyces
chemical_list: C528342:2-nitropyrrole; D000900:Anti-Bacterial Agents; D001688:Biological Products; D011758:Pyrroles; C554878:heronapyrrole A