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The Total Synthesis of (±)-Fumimycin

✍ Scribed by Dipl.-Chem. Patrick J. Gross; Prof. Dr. Stefan Bräse

Publisher
John Wiley and Sons
Year
2010
Tongue
English
Weight
300 KB
Volume
16
Category
Article
ISSN
0947-6539

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✦ Synopsis

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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