1258951-07-3Relevant academic research and scientific papers
The total synthesis of (±)-fumimycin
Gross, Patrick J.,Braese, Stefan
scheme or table, p. 12660 - 12667 (2011/02/22)
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. Peptide deformylase (PDF)-inhibitor synthesis: A strategy involving amine formation through addition to a ketimine has been successfully employed for the first total synthesis of the antibiotic agent fumimycin (see scheme).
