333383-55-4Relevant academic research and scientific papers
Synthetic access to biologically active butenolides from Streptomyces antibioticus
Grossmann,Séquin
, p. 278 - 280 (2001)
A synthetic route to a class of substituted butenolides isolated from Streptomyces antibioticus has been elaborated. The process involves coupling of the readily available menthylated furanone 5 with aldehydes.
Bioactive butenolides from Streptomyces antibioticus Tü 99: Absolute configurations and synthesis of analogs
Grossmann, Gilles,Poncioni, Marc,Bornand, Marc,Jolivet, Beno?t,Neuburger, Markus,Séquin, Urs
, p. 3237 - 3251 (2007/10/03)
The four furanones (butenolides) 1-4, which had been isolated from the fermentation broth of Streptomyces antibioticus Tü 99 and in preliminary tests had been shown to be biologically active, were synthesized by reaction of the readily available furanones 9 or 16 with 2-methylpropanal or 2-methylbutanal. In addition, a series of analogs was prepared in a similar way from 16 using different aldehydes. The hitherto unknown absolute configurations of the natural products 1-4 as well as those of all the analogs prepared were determined with Mosher's NMR method and/or X-ray crystallography. Some of the compounds synthesized proved to be active in the quorum sensing system of Chromobacterium violaceum.
