Expanding the Rubterolone Family: Intrinsic Reactivity and Directed Diversification of PKS‐derived Pyrans.
(2018) Expanding the Rubterolone Family: Intrinsic Reactivity and Directed Diversification of PKS‐derived Pyrans. Chem Eur J 24(44), 11319-11324.
We characterized three key biosynthetic intermediates of the intriguing rubterolone familiy (tropolone alkaloids) that contain a highly reactive pyran moiety (1,5-dione) and undergo spontaneous pyridine formation in the presence of primary amines. We exploited the intrinsic reactivity of the pyran moiety and isolated several new rubterolone derivatives, two of which contain a unique thiazolidine moiety. Three rubterolone derivatives were chemically modified with fluorescence and biotin tags using peptide coupling and click reaction. Overall, eight derivatives were fully characterized by HRMS/MS and 1D and 2D NMR spectroscopy and their antimicrobial, cytotoxic, anti-inflammatory and antiparasitic activities evaluated.
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doi: 10.1002/chem.201802066 PMID: 29846024