Sphingosine and clavaminol H derivatives bearing fluorinated chains and their cytotoxic activity

Microwave induced cross-metathesis of perfluoroalkylated propenes with a substituted allyl alcohol is a simple and straightforward method for the synthesis of sphingosine derivatives possessing perfluoroalkyl chains. One of the prepared compounds was converted into the fluorinated clavaminol H derivative and its deacetylated congener. Selected compounds were subjected to preliminary testing for cytotoxic activity on several cancer cell lines.

Graphical abstractSphigosines type compounds bearing perfluoroalkylated chains can be easily prepared by Ru-catalyzed cross-metathesis reactions.Figure optionsDownload full-size imageDownload as PowerPoint slideHighlights► Cross-metathesis of perfluoroalkylpropenes with functionalized alkenes. ► Synthesis of fluorinated sphingosine derivatives. ► Synthesis of fluorinated clavaminol H analogues. ► Biological activity of the prepared fluorinated clavaminol H analogues.