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The total synthesis of (±)-fumimycin.
Gross, Patrick J; Bräse, Stefan.
Afiliación
  • Gross PJ; Institut für Organische Chemie, Karlsruher Institut für Technologie (KIT), Fritz-Haber-Weg 6, 76131 Karlsruhe, Germany.
Chemistry ; 16(42): 12660-7, 2010 Nov 08.
Article en En | MEDLINE | ID: mdl-20859963
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.
Asunto(s)

Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Benzofuranos / Productos Biológicos / Amidohidrolasas / Antibacterianos Idioma: En Revista: Chemistry Asunto de la revista: QUIMICA Año: 2010 Tipo del documento: Article País de afiliación: Alemania Pais de publicación: Alemania

Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Benzofuranos / Productos Biológicos / Amidohidrolasas / Antibacterianos Idioma: En Revista: Chemistry Asunto de la revista: QUIMICA Año: 2010 Tipo del documento: Article País de afiliación: Alemania Pais de publicación: Alemania