263138-68-7Relevant articles and documents
Concise and Convergent Enantioselective Total Syntheses of (+)-and (-)-Fumimycin
Retini, Michele,Bartolucci, Silvia,Bartoccini, Francesca,Mari, Michele,Piersanti, Giovanni
, p. 12221 - 12227 (2019/10/02)
The concise and convergent total syntheses of (+)-and (-)-Fumimycin have been achieved by taking advantage of strategies for the asymmetric aza-Friedel-Crafts reaction of a highly substituted hydroquinone and N-fumaryl ketimine generated from the correspo
Synthesis of the intermediate for fumimycin: A natural peptide deformylase inhibitor
Zhou, Zhi-Wang,Li, Wei-Chao,Hu, Yu,Wang, Bin,Ren, Gang,Feng, Li-Hua
, p. 3049 - 3054 (2013/09/23)
Synthetic efforts toward the potential bacterial peptide deformylase inhibitor fumimycin are reported. The synthetic approach features a tandem Friedel-Crafts alkylation/lactonization access as key reaction to the α, α-disubstituted amino acid unit, and r
The total synthesis of (±)-fumimycin
Gross, Patrick J.,Braese, Stefan
supporting information; experimental part, 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).
