Submitted to: Synlett
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: 4/18/2000
Publication Date: N/A
Interpretive Summary: In 1995, the research group of Paulitz isolated and characterized novel antifungal metabolites from the bacterium Pseudomonas aurefaciens strain 63-28. This strain was developed as a biological agent against the soil borne root pathogens Pythium and Rhizoctonia, for use in greenhouse systems. These unique 2(5H) furanone compounds have never been reported from Pseudomonas, but similar antimicrobial compounds have been reported from plants and fungi. This paper reports on the laboratory synthesis of one of these compounds and describes its stereochemistry. The synthesized compound was compared to the naturally produced compound isolated and purified from the bacterium.
Technical Abstract: The novel antifungal butenolide fugomycin (S)-1 was synthesized starting from the enantiomerically pure building block (S)-2. Its geminal dibromo substitution pattern permits gradual carbon-carbon bond formations in a stereoselective manner. The comparison of the CD spectra of natural and synthetic material permits the assignment of the absolute configuration to fugomycin.