The Total Synthesis of (±)‐Fumimycin |
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Authors: | Dipl.‐Chem. Patrick J. Gross Prof. Dr. Stefan Bräse |
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Affiliation: | Institut für Organische Chemie, Karlsruher Institut für Technologie (KIT), Fritz‐Haber‐Weg 6, 76131 Karlsruhe (Germany), Fax: (+49)?721‐608‐8581 |
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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. |
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Keywords: | amines fumimycin inhibitors natural products total synthesis |
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