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The Total Synthesis of (±)‐Fumimycin
Authors:Dipl‐Chem Patrick J Gross  Prof Dr Stefan Bräse
Institution:Institut für Organische Chemie, Karlsruher Institut für Technologie (KIT), Fritz‐Haber‐Weg 6, 76131 Karlsruhe (Germany), Fax: (+49)?721‐608‐8581
Abstract:The antibiotic agent fumimycin has been synthesized for the first time. This natural product was found to inhibit the bacterial peptide deformylase and may represent a lead structure to a class of novel antibacterials. Our synthetic strategy towards fumimycin involved the following steps: Dakin oxidation of an aldehyde functionality, conversion of an oxime through radical fragmentation to form an N‐diphenylphosphoryl group, construction of an α‐trisubstituted amine by 1,2‐addition to a ketimine, a Claisen rearrangement with subsequent transition‐metal‐catalyzed olefin isomerization to install a propenyl chain and final amidation.
Keywords:amines  fumimycin  inhibitors  natural products  total synthesis
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