Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 16, Issue 42, Pages 12660-12667Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201001036
Keywords
amines; fumimycin; inhibitors; natural products; total synthesis
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Funding
- Foundation of German Business
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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-diphenyl-phosphoryl group, construction of an alpha-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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