Journal of Organic Chemistry
Journal of Organic Chemistry
5 years ago

Synthesis and Structural Revision of the Fungal Tetramic Acid Metabolite Spiroscytalin

Synthesis and Structural Revision of the Fungal Tetramic Acid Metabolite Spiroscytalin
Oxana Kempf, Karl Kempf, Ursula Bilitewski, Rainer Schobert, Manuel Orozco
Spiroscytalin, a natural 3-spirotetramic acid of hitherto uncertain absolute configuration, was synthesized for the first time by a one-pot Knoevenagel–IMDA reaction of an l-phenylalanine-derived tetramic acid and (R)-2-methyl-deca-6E,8E-dienal. Its absolute configuration was assigned by the known configurations of the starting compounds and by NOESY correlations. Its identity with the natural isolate was proved by the comparison of the NMR and circular dichroism spectra and of the specific optical rotations. Its absolute configuration (3R,5S,6S,7R,11S,14R) is enantiomeric to that originally proposed by the isolating group. This natural isomer of spiroscytalin showed moderate activity against Candida albicans and good activity against an export-deficient mutant of Escherichia coli.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b00727

DOI: 10.1021/acs.joc.7b00727

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