Chiral tetrahydrofuran diols (THF-diols, Figure 1) represent a characteristic structural motif in a range of biogenetically unrelated natural product families. The most prominent classes are the polyether ionophores, the annonaceous acetogenines, and some terpenoid metabolites. In addition, 2,5-disubstituted THFs constitute the central repeating unit of certain artificial ion channels. Owing to the prevalence of this structural motif in biologically active natural and non-natural compounds, a number of methods for the stereoselective synthesis of THF-diols have been developed. Strategically, the stereochemistry is often established in an initial chemical transformation (e.g. by dihydroxylation or epoxida-tion of a suitable olefinic precursor) followed by a separate cyclization reaction. For instance, biomimetic di- and polyepoxide cyclizations have been established as a powerful means for the construction of TFfF-diols and related poly ethers.
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