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  • Title: Acid rearrangment of epoxy-germacranolides and absolute configuration of 1beta,10alpha-epoxy-salonitenolide.
    Author: Rosselli S, Maggio AM, Raccuglia RA, Morris-Natschke SL, Bastow KF, Lee KH, Bruno M.
    Journal: Nat Prod Commun; 2010 May; 5(5):675-80. PubMed ID: 20521529.
    Abstract:
    The acid-catalyzed cyclization of mono epoxides of cnicin acetonide (3) was investigated. Several 6,12-eudesmanolides were obtained, and their stereochemistry established by extensive spectroscopic analyses. Chemical correlations also led to the assignment of the absolute configuration of 1beta,10alpha-epoxy-salonitenolide (13), a previously isolated natural product. The cytotoxic activities of some compounds were determined against A549 and MCF-7 tumor cell lines. The esterified germacranolides 2-6 were selectively cytotoxic against the MCF-7 breast cancer cell line.
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