Synthetic Studies on Ezomycins: Stereoselective Route to a Thymine Octosyl Nucleoside Derivative.

[摘要]：belonging to the complex peptidyl nucleoside family of antibiotics. Employing D-serine as a chiral platform, a novel synthetic route to the bicyclic octosyl nucleoside core I of the ezomycins is reported. A key step in the sequence involved a stereoselective 6-exo-trig oxymercuration-oxidn. of a strategic d-hydroxy alkene deriv., toward construction of the trans-fused furopyran ring system as present in the target products. In contrast to the known carbohydrate-based synthetic routes to the above furopyranyl fragment, the present amino acid chiral template approach is expected to offer a more flexible pathway toward potential SAR-targeted structural/stereochem. modifications of this central bicyclic nucleoside component of the ezomycins.

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