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The Total Synthesis of (±)‐Fumimycin
Author(s) -
Gross Patrick J.,
Bräse Stefan
Publication year - 2010
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201001036
Subject(s) - total synthesis , chemistry , isomerization , aldehyde , oxime , claisen rearrangement , natural product , amine gas treating , combinatorial chemistry , stereochemistry , catalysis , organic chemistry
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.