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The thuggacins have attracted much attention due to their strong antibacterial activity, particularly towards <jats:italic>Mycobacterium tuberculosis<\/jats:italic>. This study focuses on 1)\u2005thuggacin derivatives that cannot equilibrate by transacylation between the three natural thuggacins\u2005A\u2013C, 2)\u2005the roles of the thiazole ring, and 3)\u2005the hexyl side chain at C2. Semi\u2010synthetic O\u2010methylation at C17 suppressed the transacylations without a substantial loss of antibacterial activity. Exchanging the C17\u2013C25 side chain for simplified hydrophobic chains led to complete loss of antibacterial activity. Exchange of the thiazole by an oxazole ring or removal of the hexyl side chain at C2 had no substantial effect on the biological properties.<\/jats:p>","DOI":"10.1002\/chem.201405874","type":"journal-article","created":{"date-parts":[[2015,2,4]],"date-time":"2015-02-04T15:08:04Z","timestamp":1423062484000},"page":"4272-4284","source":"Crossref","is-referenced-by-count":13,"title":["Total and Semi\u2010Syntheses of Antimicrobial Thuggacin Derivatives"],"prefix":"10.1002","volume":"21","author":[{"given":"Jana","family":"Franke","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Martin","family":"Bock","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Richard","family":"Dehn","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"J\u00f6rg","family":"Fohrer","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Santosh B.","family":"Mhaske","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Antonella","family":"Migliorini","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Argyrios A.","family":"Kanakis","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Rolf","family":"Jansen","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Jennifer","family":"Herrmann","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Rolf","family":"M\u00fcller","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Andreas","family":"Kirschning","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2015,2,4]]},"reference":[{"key":"e_1_2_6_1_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200700269"},{"key":"e_1_2_6_2_2","unstructured":"\u00a0"},{"key":"e_1_2_6_3_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200704897"},{"key":"e_1_2_6_3_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200704897"},{"key":"e_1_2_6_4_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200803271"},{"key":"e_1_2_6_4_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200803271"},{"key":"e_1_2_6_5_2","unstructured":"\u00a0"},{"key":"e_1_2_6_6_2","first-page":"219","author":"Zarate\u2010Ruiz G. 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