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Plantazolicin\u2005A, a novel soil\u2010bacterium metabolite, comprises a linear array of 10 five\u2010membered rings in two pentacyclic regions that derive from ribosomal peptide synthesis followed by extensive posttranslational modification. The compound possesses potent antimicrobial activity, and is selectively active against the anthrax\u2010causing organism. A conceptually different synthesis of plantazolicin\u2005A is reported in which the key steps are the use of rhodium(II)\u2010catalyzed reactions of diazocarbonyl compounds to generate up to six of the seven oxazole rings of the antibiotic. NMR spectroscopic studies and molecular modeling reveal a likely dynamic hairpin conformation with a hinge region around the two isoleucine residues. The compound has modest activity against methicillin\u2010resistant Staphylococcus aureus (MRSA).<\/jats:p>","DOI":"10.1002\/anie.201507062","type":"journal-article","created":{"date-parts":[[2015,10,16]],"date-time":"2015-10-16T08:49:24Z","timestamp":1444985364000},"page":"15147-15151","source":"Crossref","is-referenced-by-count":22,"title":["Total Synthesis of the Posttranslationally Modified Polyazole Peptide Antibiotic Plantazolicin\u2005A"],"prefix":"10.1002","volume":"54","author":[{"given":"Hiroki","family":"Wada","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Huw E. L.","family":"Williams","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Christopher J.","family":"Moody","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2015,10,16]]},"reference":[{"key":"e_1_2_3_1_2","doi-asserted-by":"publisher","DOI":"10.1002\/jlac.18581060202"},{"key":"e_1_2_3_2_2","first-page":"469","volume":"53","author":"Couper A. S.","year":"1858","journal-title":"Ann. Chim. Phys."},{"key":"e_1_2_3_3_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00227a028"},{"key":"e_1_2_3_4_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00001a054"},{"key":"e_1_2_3_5_2","doi-asserted-by":"publisher","DOI":"10.1038\/nature13384"},{"key":"e_1_2_3_6_2","volume-title":"Modern Catalytic Methods for Organic Synthesis with Diazo Compounds","author":"Doyle M. 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