Abstract
The total synthesis of (±)-rhodinose (2) and benzoxocin 4, a model system for the glycosidic moiety of nogalomycin, are reported. The key transformation in each reaction sequence involves the cycloaddition of a nitrone with vinyltrimethylsilane to produce 5-TMS-isoxazolidines followed by fluoride-induced fragmentation of the isoxazolidines to give α,β-unsaturated aldehydes.
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