63025-35-4Relevant academic research and scientific papers
Structure-activity relationship of brominated 3-alkyl-5-methylene-2(5H)- furanones and alkylmaleic anhydrides as inhibitors of Salmonella biofilm formation and quorum sensing regulated bioluminescence in Vibrio harveyi
Steenackers, Hans P.,Levin, Jeremy,Janssens, Joost C.,Weerdt, Ami De,Balzarini, Jan,Vanderleyden, Jos,De Vos, Dirk E.,De Keersmaecker, Sigrid C.
scheme or table, p. 5224 - 5233 (2010/09/11)
A library of 25 1′-unsubstituted and 1′-bromo or 1′-acetoxy 3-alkyl-5-methylene-2(5H)-furanones and two 3-alkylmaleic anhydrides was synthesized using existing and new methods. This library was tested for the antagonistic effect against the biofilm format
Synthesis of natural fimbrolides
Haval, Kishan P.,Argade, Narshinha P.
, p. 2198 - 2202 (2008/03/28)
Starting from citraconic anhydride, a three-step approach to fimbrolide congener is reported by taking the advantage of a regioselective Grignard reaction with an anhydride, followed by a dehydrative cyclization and double bromination-dehydrobromination s
Reinvestigation of the sulfuric acid-catalysed cyclisation of brominated 2-alkyllevulinic acids to 3-alkyl-5-methylene-2(5H)-furanones
Manny, Anthony J.,Kjelleberg, Staffan,Kumar, Naresh,De Nys, Rocky,Read, Roger W.,Steinberg, Peter
, p. 15813 - 15826 (2007/10/03)
A synthesis of ethyl-, butyl-, hexyl- and dodecyl-substituted fimbrolides from alkyl-substituted levulinic acid derivatives through bromination and acid promoted lactonisation is described. The underlying reactions have been investigated using levulinic acid as a model, and the effects of varying the bromination conditions and changing acid concentration on product distribution are discussed. Dibromination proceeds best in CHCl3 and proceeds in EtOH-free CHCl3 without the complication of ester formation. Cyclisation. occurs with concomitant oxidation in 98-100% H2SO4 but gives highest yields of fimbrolides in 100% H2SO4. The formation of related beckerelide substances is also described.
